Acrylonitrile compounds

ABSTRACT

The present invention relates to acrylonitrile compounds of formula (1):[wherein, R is a C1-C6 alkyl, a C3-C7 cycloalkyl optionally substituted by a C1-C4 alkyl, a naphthyl, etc., R&lt;1 &gt;is H, a halogen, a C1-C6 alkyl, etc., A is specific 5-membered aromatic heterocyclic ring containing two hetero atoms selected from N, O and S, etc., B is H, a C1-C4 alkyl, a C2-C4 alkoxyalkyl, etc.]Said compounds are useful as agricultural chemicals, in particular insecticides and acaricides.

TECHNICAL FIELD

The present invention relates to novel acrylonitrile compounds andagricultural chemicals containing said compounds as an activeingredient. The agricultural chemicals as referred to herein includeinsecticides, acaricides, nematocides, herbicides and fungicides, etc.,and are especially insecticides, acaricides and nematocides in the fieldof agriculture, horticulture, stock farming and sanitation.

BACKGROUND ART

For acrylonitrile derivatives, WO97/40009 discloses the use thereof asagricultural chemicals.

With the long-term use of insecticides and fungicides, recently, somepests have become resistant to chemicals and are often difficult toexterminate with conventional insecticides and fungicides. Accordingly,it is an object of the present invention to provide novel insecticidesand fungicides exhibiting excellent pesticidal activities.

DISCLOSURE OF THE INVENTION

In order to solve the above-mentioned problems, the present inventorshave studied to develop compounds described below that exhibit excellentpesticidal activities, in particular exhibit the activities forextremely long term. Consequently, the inventors have completed thepresent invention.

Specifically, the present invention relates to compounds described inthe following [1] to [11] (hereinafter referred to as compounds of thepresent invention) and agricultural chemicals containing said compoundsas an active ingredient described in the following [12].

[11] Acrylonitrile compounds of formula (1):

[wherein, R is a C₁-C₆ alkyl, a C₃-C₇ cycloalkyl optionally substitutedby a C₁-C₄ alkyl, a phenyl optionally substituted by X, a naphthyl or apyridyl, R¹ is H, a halogen, a C₁-C₆ alkyl, a C₃-C₇ cycloalkyloptionally substituted by a C₁-C₄ alkyl, a C₁-C₆ alkoxy, a C₁-C₄haloalkyl, a C₂-C₆ alkoxyalkyl, CH₃OC₂H₄OCH₂, a C₂-C₆alkylsulfenylalkyl, a C₂-C₆ alkylsulfinylalkyl, a C₂-C₆alkylsulfonylalkyl, a C₁-C₃ alkyl substituted by phenyl, a phenyl,C₇-C₁₀ phenoxyalkyl, COORa, CONHRb, CONRaRb, CORa, CO(piperidyl), CN,NO₂ or CH₂J,

A is

B is H, a C₁-C₄ alkyl, a C₂-C₄ alkoxyalkyl, CH₂SCH₃, CH₂OC₂H₄OCH₃, aC₁-C₄ alkyl substituted by Rc or Rd, a tetrahydropyranyl, Si(CH₃)₃,SO₂Re, SO₂NHRb, SO₂NRaRb, C(S)NHRb, C(S)NRaRb, CH₂COORa, C(O)Rf,P(O)RgRh, P(S)RgRh, an alkali metal, an alkaline earth metal orNHRiRjRk,

X is one to three substituents as freely selected from a halogen, aC₁-C₄ alkyl, a C₁-C₄ haloalkyl, a C₁-C₄ alkoxy, a C₁-C₄ haloalkoxy, aC₁-C₄ alkylsulfenyl, a C₁-C₄ alkylsulfinyl, a C₁-C₄ alkylsulfonyl, aC₁-C₄ haloalkylsulfenyl, a C₁-C₄ haloalkylsulfinyl, a C₁-C₄haloalkylsulfonyl, NO₂, CN, a phenyl and a phenoxy, Y, Y₁ and Y₂ areeach independently of the other H, a halogen, a C₁-C₄ alkyl, a C₁-C₄haloalkyl, a C₁-C₄ alkoxy, a C₁-C₄ haloalkoxy, a C₁-C₄ alkylsulfenyl, aC₁-C₄ alkylsulfinyl, a C₁-C₄ alkylsulfonyl, a C₁-C₄ haloalkylsulfenyl, aC₁-C₄ haloalkylsulfinyl, a C₁-C₄ haloalkylsulfonyl, NO₂ or CN,

Y₃ is a C₁-C₄ alkyl or a C₁-C₄ haloalkyl,

Ra is a C₁-C₆ alkyl,

Rb is H, a C₁-C₆ alkyl, or a phenyl optionally substituted by T¹,

Rc is a phenyl optionally substituted by one or more substituents asfreely selected from a halogen, a C₁-C₄ alkyl, a C₁-C₄ alkoxy and aC₁-C₄ haloalkyl,

Rd is a benzoyl optionally substituted by one or more substituents asfreely selected from a halogen, a C₁-C₄ alkyl and a C₁-C₄ haloalkyl,

Re is a C₁-C₄ alkyl, a C₁-C₄ haloalkyl, or a phenyl optionallysubstituted by T¹,

Rf is a C₁-C₆ alkyl, a C₂-C₆ alkenyl, a C₁-C₆ haloalkyl, a C₂-C₄alkoxyalkyl, a C₃-C₆ halocycloalkyl, a C₁-C₄ alkyl substituted by Rc, aC₃-C₇ cycloalkyl optionally substituted by a C₁-C₄ alkyl, a cycloalkylsubstituted by Rc, a cyclopropyl substituted by Rc and a C₁-C₄ alkyl, aC₃-C₄ cycloalkyl substituted by Rc and a halogen, a cyclopropylsubstituted by T² and a C₁-C₄ alkyl, a C₂-C₄ alkenyl substituted by Rc,a C₁-C₆ alkoxy, a C₁-C₄ haloalkoxy, a C₂-C₅ alkenyloxy, a C₃-C₆cycloalkoxy optionally substituted by a C₁-C₃ alkyl, a benzyloxy, COORa,—NU¹U², a phenyl optionally substituted by T³, a naphthyl, a pyridyloptionally substituted by T¹, a phenyl C₁-C₆ alkyl or A-1 to A-151,

Rg and Rh are each independently of the other OH, a phenyl, a C₁-C₆alkyl, a C₁-C₆ alkoxy or a C₁-C₄ alkylsulfenyl,

Ri, Rj and Rk are each independently of the other H, a C₁-C₆ alkyl, aC₁-C₄ alkenyl, a C₃-C₆ cycloalkyl optionally substituted by a C₁-C₃alkyl or a benzyl, or any two of Ri, Rj and Rk may, together with thenitrogen atom to which they are bonded, form a 5- to 8-membered ringgroup optionally containing an oxygen atom, a nitrogen atom or a sulfuratom,

J is a pyrazolyl, an imidazolyl or a morpholinyl,

T¹ is a halogen, a C₁-C₄ alkyl, a C₁-C₄ haloalkyl or a C₁-C₄ alkoxy,

T² is a C₂-C₄ alkenyl optionally substituted by a halogen,

T³ is one to five substituents as freely selected from a halogen, aC₁-C₄ alkyl, a C₁-C₄ haloalkyl, a C₁-C₄ alkoxy, a C₁-C₄ haloalkoxy, aC₁-C₄ alkylsulfenyl, a C₁-C₄ alkylsulfinyl, a C₁-C₄ alkylsulfonyl, aC₁-C₄ haloalkylsulfenyl, a C₁-C₄ haloalkylsulfinyl, a C₁-C₄haloalkylsulfonyl, NO₂, CN, CHO, —NU¹U², a phenyl and a phenoxy,

U¹ and U² are each independently of the other H, a C₁-C₆ alkyl, COORa, aphenyl or a benzyl, or U¹ and U² may, together with the nitrogen atom towhich they are bonded, form a 5- to 8-membered ring group optionallycontaining an oxygen atom, a nitrogen atom or a sulfur atom,

m represents the number of substituents, and is 0, 1, 2 or 3,

n represents the number of substituents, and is 0, 1, 2, 3 or 4,

p represents the number of substituents, and is 0, 1 or 2,

q represents the number of substituents, and is 0 or 1,

(provided that when m, n or p is 2 or more, then the substituents may bethe same or different)].

[2] Acrylonitrile compounds of the above-mentioned [1], in which A is

[3] Acrylonitrile compounds of the above-mentioned [2], in which R is

1-naphtyl, tertiary butyl or 2-pyridyl,

X₁ is H, a halogen, a C₁-C₄ alkyl, a C₁-C₄ alkoxy, a C₁-C₄ haloalkyl ora phenyl,

X₂ is H or a halogen,

R¹ is H, a C₁-C₆ alkyl, a C₃-C₇ cycloalkyl, CN, COORa, CO(N-piperidyl),a C₂-C₆ alkylsulfenylalkyl, a C₂-C₆ alkoxyalkyl, CH₃OC₂H₄OCH₂, CONRaRb,a phenyl or CH₂J,

A is A-1, A-2, A-3, A-6 or A-7,

B is H, a C₁-C₄ alkyl, C(O)Rf, SO₂Re or a C₂-C₄ alkoxyalkyl,

Ra and Rb are each independently of the other a C₁-C₆ alkyl,

Rf is a C₁-C₆ alkyl, a C₁-C₆ alkoxy, a phenyl optionally substituted bya halogen, 2-pyridyl, 3-pyridyl, a phenyl C₁-C₆ alkyl or 5-pyrazolylsubstituted by a C₁-C₄ alkyl,

Re is a C₁-C₄ alkyl or a phenyl,

Y₁ and Y₂ are each independently of the other H, a halogen, a C₁-C₄alkyl, a C₁-C₄ haloalkyl or CN,

Y₃ is a C₁-C₄ alkyl,

J is an N-pyrazolyl or N-morpholinyl.

[4] Acrylonitrile compounds of the above-mentioned [3], in which R is

X₁ is H, a halogen, a C₁-C₄ alkyl, a C₁-C₄ alkoxy, a C₁-C₄ haloalkyl ora phenyl,

X₂ is H or a halogen,

R¹ is H, a C₁-C₆ alkyl, a C₃-C₇ cycloalkyl, CN, COORa, CO(N-piperidyl),a C₂-C₆ alkylsulfenylalkyl, a C₂-C₆ alkoxyalkyl, CH₃OC₂H₄OCH₂, CONRaRb,a phenyl or CH₂J,

A is A-1,

B is H, a C₁-C₄ alkyl, C(O)Rf, SO₂Re or a C₂-C₄ alkoxyalkyl,

Ra and Rb are each independently of the other a C₁-C₆ alkyl,

Rf is a C₁-C₆ alkyl, a C₁-C₆ alkoxy, a phenyl substituted by a halogen,2-pyridyl, 3-pyridyl, a phenyl C₁-C₆ alkyl or 5-pyrazolyl substituted bya C₁-C₄ alkyl,

Re is a C₁-C₄ alkyl or a phenyl,

Y₁ is H, a halogen, a C₁-C₄ alkyl or CN,

Y₂ is H, a halogen or a C₁-C₄ alkyl,

Y₃ is a C₁-C₄ alkyl,

J is an N-pyrazolyl or N-morpholinyl.

[5] Acrylonitrile compounds of the above-mentioned [4], in which X₁ isH, a fluorine atom, a chlorine atom, a bromine atom, methyl, methoxy,trifluoromethyl or a phenyl,

X₂ is H, a fluorine atom or a chlorine atom,

R¹ is H, methyl, ethyl, normal propyl, isopropyl, normal butyl, normalhexyl, cyclohexyl, CN, COORa, CO(N-piperidyl), methylsulfenylmethyl,methoxymethyl, ethoxymethyl, normal butoxymethyl, CH₃OC₂H₄OCH₂, CONRaRb,a phenyl, CH₂(N-pirazolyl) or CH₂(N-morpholinyl),

B is H, methyl, C(O)Rf, SO₂Re, methoxymethyl or ethoxymethyl,

Ra and Rb are methyl,

Rf is tertiary butyl, ethoxy, isobutoxy, 2-chlorophenyl, 2-pyridyl,3-pyridyl, benzyl, or 1,3,4-trimethyl-5-pyrazolyl,

Re is methyl or phenyl,

Y₁ is H, a chlorine atom, methyl or CN,

Y₂ is H, a bromine atom, methyl or ethyl,

Y₃ is methyl.

[6] Acrylonitrile compounds of the above-mentioned [4], in which X₁ isH, a halogen or a C₁-C₄ alkyl,

X₂ is H or a halogen,

R¹ is a C₁-C₆ alkyl,

B is C(O)Rf,

Rf is a C₁-C₆ alkyl,

Y₁ is a halogen or a C₁-C₄ alkyl,

Y₂ is a C₁-C₄ alkyl,

Y₃ is a C₁-C₄ alkyl.

[7] Acrylonitrile compounds of the above-mentioned [6], in which X₁ isH, a fluorine atom, a chlorine atom, a bromine atom or methyl,

X₂ is H or a fluorine atom,

R¹ is methyl, ethyl, normal propyl, isopropyl or normal butyl,

B is C(O)Rf,

Rf is tertiary butyl,

Y₁ is a chlorine atom or methyl,

Y₂ is methyl,

Y₃ is methyl.

[8] Acrylonitrile compounds of the above-mentioned [3], in which R is

X₁ is H, a halogen or a C₁-C₄ alkyl,

R¹ is H, a C₁-C₆ alkyl or a C₃-C₇ cycloalkyl,

A is A-3,

B is H or C(O)Rf,

Rf is a C₁-C₆ alkyl, a phenyl or a phenyl C₁-C₆ alkyl,

Y₁ is a C₁-C₄ alkyl or a C₁-C₄ haloalkyl,

Y₂ is a C₁-C₄ alkyl.

[9] Acrylonitrile compounds of the above-mentioned [8], in which X₁ isH, a chlorine atom or methyl,

R¹ is H, methyl, ethyl, isopropyl, normal butyl or cyclohexyl,

B is H or C(O)Rf,

Rf is tertiary butyl, a phenyl or a benzyl,

Y₁ is methyl or trifluoromethyl,

Y₂ is methyl.

[10] Acrylonitrile compounds of the above-mentioned [8], in which X₁ isH,

R¹ is a C₁-C₆ alkyl,

B is C(O)Rf,

Rf is a C₁-C₆ alkyl,

Y₁ is a C₁-C₄ alkyl,

Y₂ is a C₁-C₄ alkyl.

[11] Acrylonitrile compounds of the above-mentioned [10], in which X₁ isH,

R¹ is methyl, ethyl, isopropyl or normal butyl,

B is C(O)Rf,

Rf is tertiary butyl,

Y₁ is methyl,

Y₂ is methyl.

[12] An agricultural chemical characterized by comprising, as an activeingredient, one or more acrylonitrile compounds of any one of theabove-mentioned [1] to [11].

The compounds of the above-mentioned [3] are preferable in the terms ofexcellent residual effect, the compounds of the above-mentioned [4] and[8] are more preferable, the compounds of the above-mentioned [5], [6],[9] and [10] are further more preferable, and the compounds of theabove-mentioned [7] and [11] are the most preferable.

The moiety —C(CN)═C(OB) of the compounds (1) of the present inventionincludes two isomers of E-form and Z-form, both of which are within thescope of the present invention.

Now, preferred scopes of R, R¹, A, B, X, Y, Ra, Rb, Rc, Rd, Re, Rf, Rg,Rh, Ri, Rj, Rk, T¹, T³, Y₁, Y₂, Y₃, U¹, U², m, n, p or q are referred tohereunder.

The preferred scope of R is the following group.

RI: C₁-C₆ alkyl, phenyl optionally substituted by X, pyridyl.

RII: C₁-C₆ alkyl, phenyl optionally substituted by X.

The preferred scope of R¹ is the following group.

R¹I: H, C₁-C₆ alkyl, C₂-C₆ alkoxyalkyl, CH₃OC₂H₄OCH₂, C₂-C₆alkylsulfenylalkyl.

R¹II: H, C₁-C₆ alkyl.

The preferred scope of A is the following group.

AI: A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8.

AII: A-1, A-3, A-4, A-5, A-6, A-7, A-8.

AIII: A-1, A-3.

The preferred scope of B is the following group.

BI: H, C₁-C₄ alkyl, C₂-C₄ alkoxyalkyl, CH₂OC₂H₄OCH₃, SO₂Re, SO₂NHRb,SO₂NRaRb, C(S)NHRb, C(S)NRaRb, CH₂COORa, C(O)Rf, alkali metal, alkalineearth metal, NHRiRjRk.

BII: H, C₁-C₄ alkyl, C₂-C₄ alkoxyalkyl, SO₂Re, C(O)Rf, alkali metal,alkaline earth metal, NHRiRjRk.

BIII: H, C₁-C₄ alkyl, C₂-C₄ alkoxyalkyl, SO₂Re, C(O)Rf.

The preferred scope of X is the following group.

XI: one to three substituents as freely selected from halogen, C₁-C₄alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and phenyl.

XII: one to two substituents as freely selected from halogen, C₁-C₄alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and phenyl.

The preferred scope of Y is the following group.

YI: one to three substituents as freely selected from H, halogen, C₁-C₄alkyl, C₁-C₄ haloalkyl, C¹-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylsulfenyl, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄haloalkylsulfenyl, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl andCN.

YII: one to three substituents as freely selected from H, halogen, C₁-C₄alkyl and C₁-C₄ haloalkyl.

The preferred scope of Ra is the following group.

RaI: C₁-C₄ alkyl.

The preferred scope of Rb is the following group.

RbI: C₁-C₆ alkyl, phenyl optionally substituted by T¹.

The preferred scope of Rc is the following group.

RcI: halogen, C₁-C₄ alkyl, phenyl optionally substituted by C₁-C₄alkoxy.

The preferred scope of Rd is the following group.

RdI: halogen, benzoyl optionally substituted by C₁-C₄ alkyl.

The preferred scope of Re is the following group.

ReI: C₁-C₄ alkyl, phenyl optionally substituted by T¹.

The preferred scope of Rf is the following group.

RfI: C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₄ alkoxyalkyl,C₃-C₆ cycloalkyl optionally substituted by C₁-C₃ alkyl, C₁-C₆ alkoxy,C₃-C₆ cycloalkoxy, phenyl optionally substituted by T³.

RfII: C₁-C₆ alkyl, C₃-C₆ cycloalkyl optionally substituted by C₁-C₃alkyl, C₁-C₆ alkoxy, phenyl optionally substituted by T³.

The preferred scope of Rg is the following group.

RgI: OH, phenyl, C₁-C₆ alkoxy, C₁-C₄ alkylsulfenyl.

The preferred scope of Rh is the following group.

RhI: C₁-C₆ alkoxy, C₁-C₄ alkylsulfenyl.

The preferred scope of Ri is the following group.

RiI: H, C₁-C₆ alkyl, C₃-C₆ cycloalkyl or benzyl, or Ri and Rj may,together with the nitrogen atom to which they are bonded, form a 5- to6-membered ring group optionally containing an oxygen atom, a nitrogenatom or a sulfur atom.

The preferred scope of Rj is the following group.

RjI: H, C₁-C₆ alkyl, C₃-C₆ cycloalkyl or benzyl, or Ri and Rj may,together with the nitrogen atom to which they are bonded, form a 5- to6-membered ring group optionally containing an oxygen atom, a nitrogenatom or a sulfur atom.

The preferred scope of Rk is the following group.

RkI: H, C₁-C₆ alkyl.

The preferred scope of U¹ is the following group.

U¹I: H, C₁-C₆ alkyl, COORa, phenyl or benzyl.

The preferred scope of U² is the following group.

U²I: H, C₁-C₆ alkyl, COORa, phenyl or benzyl.

In addition, it is also preferable that U¹ and U² together with thenitrogen atom to which they are bonded, form a 5- to 8-membered ringgroup optionally containing an oxygen atom, a nitrogen atom or a sulfuratom.

The preferred scope of T¹ is the following group.

T¹I: halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl.

The preferred scope of T³ is the following group.

T³I: one to three substituents as freely selected from halogen, C₁-C₄alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylsulfenyl, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, —NU¹U².

T³II: one to three substituents as freely selected from halogen, C₁-C₄alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy.

The preferred scope of Y₁ is the following group.

Y₁I: H, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl.

The preferred scope of Y₂ is the following group.

Y₂I: H, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylsulfenyl, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄ haloalkylsulfenyl, C₁-C₄ haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl.

Y₂II: H, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl.

The preferred scope of Y₃ is the following group.

Y₃I: C₁-C₄ alkyl.

The preferred scope of m is 1, 2 or 3, and more preferably is 1 or 2.

The preferred scope of n is 0, 1, 2 or 3, and more preferably is 1 or 2.

The preferred scope of p is 1 or 2.

The above-mentioned preferred groups in the scopes of the preferredsubstituents can be optionally combined. Hereunder mentioned areespecially preferred compounds of the present invention.

Compounds of the invention comprising preferred substituents of RI, R¹I,AI, BI, XI, YI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I, U²I,Y₁I, Y₂I and Y₃I.

Compounds of the invention comprising preferred substituents of RI, R¹I,AII, BI, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I, U²I, Y₁I,Y₂I and Y₃I.

Compounds of the invention comprising preferred substituents of RI, R¹I,AIII, BI, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I, U²I,Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RI, R¹I,AIII, BI, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I, U²1,Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AI, BI, XI, YI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AII, BI, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I, U²I,Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AIII, BI, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RI, R¹I,AII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I, U²I,Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RI, R¹I,AII, BIII, XI, RaI, RbI, ReI, RfI, T¹I, T³I, U¹I, U²I, Y₁I, Y₂II andY₃I.

Compounds of the invention comprising preferred substituents of RI, R¹I,AIII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I, U²I,Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RI, R¹I,AIII, BIII, XI, RaI, RbI, ReI, RfI, T¹I, T³I, U¹I, U²I, Y₁I, Y₂II andY₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AII, BIII, XI, RaI, RbI, ReI, RfI, T¹I, T³I, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AIII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AIII, BIII, XI, RaI, RbI, ReI, RfI, T¹I, T³I, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AII, BIII, XI, RaI, RbI, ReI, RfI, T¹I, T³I, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AIII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AIII, BIII, XI, RaI, RbI, ReI, RfI, T¹I, T³I, U¹, U²I, Y₁, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AII, BIII, XI, RaI, RbI, ReI, RfI, T¹I, T³I, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AIII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AIII, BIII, XI, RaI, RbI, ReI, RfI, T¹I, T³I, U₁I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AII, BII, XI, RaI, RbI, ReI, RfII, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³I, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AIII, BII, XI, RaI, RbI, ReI, RfII, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AIII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³I, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AII, BII, XI, RaI, RbI, ReI, RfII, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³I, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AIII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AIII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³I, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³I, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AIII, BII, XI, RaI, RbI, ReI, RfII, RiI, RjI, RkI, T¹I, T³I, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AIII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³I, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AII, BII, XI, RaI, RbI, ReI, RfII, RiI, RjI, RkI, T¹I, T³II, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³I, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AIII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³II, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹I, AIII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³II, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AII, BII, XI, RaI, RbI, ReI, RfII, RiI, RjI, RkI, T¹I, T₃II, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³II, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AIII, BII, XI, RaI, RbI, ReI, RfII, RiI, RjI, RkI, T¹I, T³II, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RI,R¹II, AIII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³II, U¹I, U²I, Y₁I,Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AII, BII, XI, RaI, RbI, ReI, RfI, RiI, RjI, RkI, T¹I, T³II, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³II, U¹I, U²I, Y₁I, Y₂IIand Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AIII, BII, XI, RaI, RbI, ReI, RfII, RiI, RjI, RkI, T¹I, T³II, U¹I,U²I, Y₁I, Y₂II and Y₃I.

Compounds of the invention comprising preferred substituents of RII,R¹II, AIII, BIII, XI, RaI, RbI, ReI, RfII, T¹I, T³II, U¹I, U²I, Y₁I,Y₂II and Y₃I.

Now, specific examples of atoms and groups in the definitions of R, R¹,A, B, X, Y, Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri, Rj, Rk, T¹, T², T³, Y₁,Y₂, Y₃, U¹ and U² are mentioned below.

The halogen atom for R¹, X, Y, Rc, Rd, T¹, T², T³, Y₁ and Y₂ includes afluorine atom, a chlorine atom, a bromine atom and an iodine atom.Preferred are a fluorine atom, a chlorine atom and a bromine atom.

The alkyl for R, R¹, B, X, Y, Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri, Rj,Rk, T¹, T³, Y₁, Y₂, Y₃, U¹ and U² may be a straight chain or branchedalkyl group having indicated carbon atoms, which includes, for example,methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl,sec-butyl, pentyl-1, pentyl-2, pentyl-3, 2-methylbutyl-1,2-methylbutyl-2, 2-methylbutyl-3, 3-methylbutyl-1, 2,2-dimethylpropyl-1,hexyl-1, hexyl-2, hexyl-3, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and1-ethyl-2-methylpropyl, etc.

The haloalkyl for R¹, X, Y, Rc, Rd, Re, Rf, T¹, T³, Y₁, Y₂ and Y₃ may bea straight chain or branched haloalkyl group having indicated carbonatoms, which includes, for example, fluoromethyl, chloromethyl,bromomethyl, fluoroethyl, chloroethyl, bromoethyl, fluoro-n-propyl,chloro-n-propyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl,dichloromethyl, trichloromethyl, difluoroethyl, trifluoroethyl,trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl,trifluorochloroethyl, hexafluoro-n-propyl, chlorobutyl and fluorobutyl,etc.

The C₃-C₇ cycloalkyl optionally substituted by a C₁-C₄ alkyl for R, Rf,Ri, Rj and Rk includes, for example, cyclopropyl, 1-methylcyclopropyl,2,2,3,3-tetramethylcyclopropyl, cyclobutyl, 1-ethylcyclobutyl,1-n-butylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl,1-methylcyclohexyl and 4-methylcyclohexyl, cycloheptyl, etc.

The C₁-C₄ alkyl optionally substituted by Rc for Rf includes, forexample, benzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-chlorobenzyl,4-methylbenzyl, 4-tertiary butylbenzyl, 2-methylbenzyl, 2-methoxybenzyl,1-phenylethyl, 1-(3-chlorophenyl)ethyl, 2-phenylethyl,1-methyl-1-phenylethyl, 1-(4-chlorophenyl)-1-methylethyl,1-(3-chlorophenyl)-1-methylethyl, 1-phenylpropyl, 2-phenylpropyl,3-phenylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl,4-phenylbutyl, 1-methyl-1-phenylpropyl, 1-methyl-2-phenylpropyl,1-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl,2-(4-chlorophenyl)-2-methylpropyl and 2-methyl-2-(3-methylphenyl)propyl,etc.

The phenyl optionally substituted by T¹ for Rb and Re includes, forexample, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl,2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl,3-bromophenyl, 4-bromophenyl, 4-iodophenyl, 2,4-dichlorophenyl,3,4-dichlorophenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl,2-fluoro-4-chlorophenyl, 2,3,4,5,6-pentafluorophenyl, 2-methylphenyl,3-methylphenyl, 4-methylphenyl, 2,5-dimethylphenyl,4-methyl-2,3,5,6-tetrafluorophenyl, 2-methoxyphenyl, 3-methoxyphenyl,4-methoxyphenyl, 2,6-methoxyphenyl, 3,4-dimethoxyphenyl and3,4,5-trimethoxyphenyl, 2-trifluoromethylphenyl,3-trifluoromethylphenyl, 4-trifluoromethylphenyl, etc.

The alkoxy for R¹, X, Y, Rc, Rf, Rg, Rh, T¹, T³, Y₁ and Y₂ may be astraight chain or branched alkoxy having indicated carbon atoms, whichincludes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy,isobutoxy, sec-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy,1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy,1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,1-ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy,3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy,1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy,2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy,2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy,1-ethyl-1-methylpropyloxy and 1-ethyl-2-methylpropyloxy, etc.

The —NU¹U² for Rf and T³ includes, for example, methylamino, ethylamino,n-propylamino, isopropylamino, n-butylamino, isobutylamino,sec-butylamino, tert-butylamino, n-pentylamino, 1-methylbutylamino,2-methylbutylamino, 3-methylbutylamino, 1,1-dimethylpropylamino,1,2-dimethylpropylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino,n-hexylamino, 1-methylpentylamino, 2-methylpentylamino,3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino,1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino,2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino,2-ethylbutylamino, 1,1,2-trimethylpropylamino,1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino, dimethylamino,diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino,di-sec-butylamino, diisobutylamino, di-n-pentylamino, di-n-hexylamino,methylethylamino, methylpropylamino, methylisopropylamino,methylbutylamino, methyl-sec-butylamino, methylisobutylamino,methyl-tert-butylamino, methylpentylamino, methylhexylamino,ethylpropylamino, ethylisopropylamino, ethylbutylamino,ethyl-sec-butylamino, ethylisobutylamino, ethylpentylamino,ethylhexylamino, phenylamino, benzylamino, N-acetamide,N-ethylacetamide, N-phenylacetamide and N-acetylacetamide, etc., towhich is applied the indicated scope of the carbon atoms constitutingit.

The haloalkoxy for X, Y, Rf, T³, Y₁ and Y₂ may be a straight chain orbranched haloalkoxy, which includes, for example, fluoromethoxy,difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy,dichloromethoxy, trichloromethoxy, bromomethoxy, fluoroethoxy,chloroethoxy, bromoethoxy, difluoroethoxy, trifluoroethoxy,tetrafluoroethoxy, pentafluoroethoxy, trichloroethoxy,trifluorochloroethoxy, fluoropropoxy, chloropropoxy, bromopropoxy,fluorobutoxy, chlorobutoxy, fluoro-iso-propoxy, chloro-iso-propoxy, etc.

The C₁-C₄ alkylsulfenyl for X, Y, Rg, Rh, T³, Y₁ and Y₂ includes, forexample, methylthio, ethylthio, n-propylthio, iso-propylthio,n-butylthio, iso-butylthio, sec-butylthio and tert-butylthio, etc.

The C₁-C₄ alkylsulfinyl for X, Y, T³, Y₁ and Y₂ includes, for example,methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl,n-butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl andtert-butylsulfinyl, etc.

The C₁-C₄ alkylsulfonyl for X, Y, T³, Y₁ and Y₂ includes, for example,methyl sulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl,n-butylsulfonyl, iso-butylsulfonyl, sec-butylsulfonyl andtert-butylsulfonyl, etc.

The C₂-C₄ alkoxyalkyl for R¹, B and Rf includes, for example,methoxymethyl, ethoxymethyl, n-propoxymethyl, i-propoxymethyl,n-butoxymethyl, i-butoxymethyl, s-butoxymethyl, t-butoxymethyl,n-pentyloxymethyl, methoxyethyl, ethoxymethyl and methoxypropyl, etc.,to which is applied the indicated scope of the carbon atoms constitutingit.

The C₂-C₆ alkylsulfenylalkyl for R¹ includes, for example,methylthiomethyl, ethylthiomethyl, n-propylthiomethyl,i-propylthiomethyl, n-butylthiomethyl, i-butylthiomethyl,s-butylthiomethyl, t-butylthiomethyl, n-pentylthiomethyl,methylthioethyl, ethylthiomethyl and methylthiopropyl, etc.

The naphthyl for R and Rf includes, for example, 1-naphtyl and2-naphtyl.

The haloalkylsulfenyl for X, Y, T³, Y₁ and Y₂ may be a straight chain orbranched C₁-C₄ haloalkylthio, including, for example, fluoromethylthio,chlorodifluoromethylthio, bromodifluoromethylthio, trifluoromethylthio,trichloromethylthio, 2,2,2-trifluoroethylthio,1,1,2,2-tetrafluoroethylthio, fluoroethylthio, pentafluoroethylthio andfluoro-iso-propylthio, etc.

The haloalkylsulfinyl for X, Y, T³, Y₁ and Y₂ may be a straight chain orbranched C₁-C₄ haloalkylsulfinyl, including, for example,fluoromethylsulfinyl, chlorodifluoromethylsulfinyl,bromodifluoromethylsulfinyl, trifluoromethylsulfinyl,trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl,1,1,2,2-tetrafluoroethylsulfinyl, fluoroethylsulfinyl,pentafluoroethylsulfinyl and fluoro-iso-propylsulfinyl, etc.

The haloalkylsulfonyl for X, Y, T³, Y₁ and Y₂ may be a straight chain orbranched C₁-C₄ haloalkylsulfonyl, including, for example,fluoromethylsulfonyl, chlorodifluoromethylsulfonyl,bromodifluoromethylsulfonyl, trifluoromethylsulfonyl,trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,1,1,2,2-tetrafluoroethylsulfonyl, fluoroethylsulfonyl,pentafluoroethylsulfonyl and fluoro-iso-propylsulfonyl, etc.

The alkenyloxy for Rf may be a straight chain or branched C₂-C₄alkenyloxy, including, for example, allyloxy, 2-propenyloxy,2-butenyloxy and 2-methyl-2-propenyloxy, etc.

The C₁-C₄ alkenyl for Ri, Rj and Rk includes, for example, allyl,2-propenyl, 2-butenyl, 2-methyl-2-propenyl, 4-methyl-3-pentenyl and2-hexenyl, etc, to which is applied the indicated scope of the carbonatoms constituting it.

The alkali metal for B includes, for example, lithium, sodium andpotassium.

The alkaline earth metal for B includes, for example, magnesium,calcium, strontium or barium, preferably magnesium, calcium or barium.

The NHRiRjRk for B includes, for example, asmmonium group,monomethylammonium group, dimethylammonium group, trimethylammoniumgroup, diethylammonium group, triethylammonium group,diisopropylammonium group, diisopropylethylammonium group,hexylmethylammonium group, cyclopropylmethylammonium group,cyclohexylmethylammonium group, allylmethylammonium group,benzylmethylammonium group or 4-methylcyclohexylethylammonium group, orany two of Ri, Rj and Rk together with the nitrogen atom to which theyare bonded, form a heterocyclic 5-, 6-, 7- or 8-membered ammonium groupoptionally containing an oxygen atom, a nitrogen atom or a sulfur atom.

For Ri, Rj and Rk, the heterocyclic 5- to 8-membered ammonium groupoptionally containing an oxygen atom, a nitrogen atom or a sulfur atom,which is formed by any two of Ri, Rj and Rk together with the nitrogenatom to which they are bonded, includes, for example, pyrrolidine,pyrazolidine, imidazolidine, oxazolidine, isoxazolidine, thiazolidine,piperidine, piprerazine, morpholine, thiamorpholine, hexamethyleneimineand heptamethylenimine, etc.

For U¹ and U², the heterocyclic 5- to 8-membered ring optionallycontaining an oxygen atom, a nitrogen atom or a sulfur atom, which isformed by U¹ and U² together with the nitrogen atom to which they arebonded, includes, for example, pyrrolidine, pyrazolidine, imidazolidine,oxazolidine, isoxazolidine, thiazolidine, piperidine, piprerazine,morpholine, thiamorpholine, hexamethyleneimine and heptamethylenimine,etc.

The C₃-C₆ halocycloalkyl for Rf includes, for example,fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl,dichlorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, chlorocyclobutyl,dichlorocyclobutyl, chlorocyclopentyl, dichlorocyclopentyl,chlorocyclohexyl, dichlorocyclohexyl and tetrafluorocyclobutyl, etc.

The cyclopropyl optionally substituted by T² and C₁-C₄ alkyl for Rfincludes, for example, 2,2-dimethyl-3-(2,2-dimethylethenyl)cyclopropyl,3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropyl,3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropyl and3-(2,2-chlorotrifluoroetheny)-2,2-dimethylcyclopropyl, etc.

The C₃-C₆ cycloalkoxy optionally substituted by C₁-C₄ alkyl for Rfincludes, for example, cyclopropoxy, cyclobutoxy, cyclopentoxy,cyclohexyloxy, 1-methylcyclopropoxy, etc.

The C₃-C₄ cycloalkyl substituted by Rc and halogen atom for Rf includes,for example, 2,2-dichloro-1-phenylcyclopropyl,2,2-dichloro-1-(3-chlorophenyl)cyclopropyl,2,2-dichloro-1-(4-methoxyphenyl)cyclopropyl,2,2-dichloro-1-(4-ethoxyphenyl)cyclopropyl,2,2-dichloro-1-(4-i-propyloxyphenyl)cyclopropyl,2,2-dichloro-1-(4-t-butylphenyl)cyclopropyl,2,2-dichloro-1-(4-methoxyphenyl)-3-phenylcyclopropyl and1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorobutyl, etc.

The cyclopropyl substituted by Rc and C₁-C₄ alkyl for Rf includes, forexample, 2,2-dimethyl-1-phenylcyclopropyl,1-(4-chlorophenyl)-2,2-dimethylcyclopropyl,2,2-dimethyl-3-phenylcyclopropyl,3-(3-chloropheny)-2,2-dimethylcyclopropyl,(4-chlorophenyl)-2,2-dimethyl-3-phenylcyclopropyl,(4-bromophenyl)-2,2-dimethyl-3-phenylcyclopropyl,2,2-dimethyl-3-(4-methylphenyl) cyclopropyl and (4-tertiarybutylphenyl)-2,2-dimethyl-3-phenylcyclopropyl, etc.

The C₃-C₆ cycloalkyl substituted by Rc for Rf includes, for example,1-phenylcyclopropyl, 1-(3-chlorophenyl)cyclopropyl,1-(4-chlorophenyl)cyclopropyl, 1-(4-bromophenyl)cyclopropyl,1-(4-fluorophenyl)cyclopropyl, 1-(4-ethylphenyl)cyclopropyl,1-(4-propylphenyl)cyclopropyl, 2-phenylcyclopropyl, 1-phenylcyclobutyl,2-phenylcyclobutyl, 1-phenylcyclopentyl, 1-(4-chlorophenyl)cyclopentyl,3-phenylcyclopentyl, 1-phenylcyclohexyl, 1-(3-fluorophenyl)cyclohexyl,1-(4-chlorophenyl)cyclohexyl, 1-(4-tertiary butylphenyl)cyclohexyl,2-phenylcyclohexyl, 3-phenylcyclohexyl and 4-phenylcyclohexyl, etc.

Even at low concentration, the compounds of the present inventioneffectively prevent various pests, which include, for example, so-calledagricultural insect pests that injure agricultural and horticulturalcrops and trees, so-called livestock insects that live on livestock andpoultry, so-called sanitary insect pests that have various negativeinfluences on the human living environment including houses, so-calledstored products pests that injure grains stored in storehouses, and alsoacarids, nematodes, molluscs and crustaceans that live in the same sitesas above and injure those mentioned above.

Examples of the insect pests, acarids, nematodes, molluscs andcrustaceans capable of being exterminated by the compounds of thepresent invention are mentioned below, which , however, are notlimitative.

Insect pests of Lepidoptera, such as rice stem borer (Chilosuppressalis), rice leafroller (Cnaphalocrocis medinalis), green ricecatapillar (Neranga aenescens), rice skipper (Pamara guttata), diamondback moths (Plutella xylostella), cabbage armyworms (Mamestrabrassicae), common white (Pieris rapae cnucivora), turnip moth (Agrotissegetum), common cutworm (Spodptera litura), beet armyworm (Spodpteraexigua), tabacco budwarm (Helicoverpa armigera), smaller tea tortrix(Adoxophyes sp.), oriental tea tortrix (Homona magnanima), peach fruitmoth (Carposina niponensis), oriental fruit moth (Grapholita molesta),summer fruit tortrix (Adoxophyes orana fasciata), apple leafminers(Phyllonorycter ringoniella), corn earwarm (Helicoverpa zea), tobaccobudworm (Heliothis virescens), European corn borer (Ostrinia nubialis),fall armyworm (Spodoptera frugiperda), Coding moth (Cydia pomonella),fall webworms (Hyphantria cunea), etc.:

Insect pestd of Hemiptera, such as green rice leafhopper (Nephotettixcincticeps), brown rice planthoppers (Nilaparvata lugens), green peachaphid (Myzus persicae), cotton aphid (Aphis gossypii), greenhousewhitefly (Trialeurodes vaporariorum), sweetpotato white fly (Bemisiatabaci), pear psylla (Psylla pyricola), azalea lace bug (Stephantispyriodes), arrowhead scale (Unaspis yanonensis), comstock mealybug(Pseudococcus comstocki), red wax scale (Ceroplastes rubens), giantmealybug (Drosicha corpulenta), brown-marmorated stinkbug (Halyomorphamista), cabbage bug (Eurydema rugosam), bed bug (Cimex lectularis),etc.;

Insect pests of Coleoptera, such as twenty-eight-spotted ladybird(Henosepilachna vigintioctopunctata), cupreous chafers (Anomala cuprea),Japanese beetle (Popilla japonica), ricewater weevil (Lissorhoptrusoryzophilus), hunting billbug (Sphenophrus venatus vestitus),sweetpotato weevil (Cylas formicarius), cucurbit leaf beetle(Aulacophora femoralis), striped flea beetle (Phyllotreta striolata),Colorado potato beetle (Leptinotarsa decemlineata), white-spottedlongicorn beetle (Anoplophora malasiaca), Paederus fuscipes, pinesawyers (Monochamus altematus), sugarcane wire worm (Melanotustamsuyensis), Europea domina, corn rootworms (Diabrotica spp.), lesserrice weevil (Sitophilus oryzae), granary weevils (Sitophilus granarius),red four beetle (Tribolium castaneum), etc.;

Insect pests of Diptera, such as legume leafminer (Liriomyza trifoli),seedcorn maggot (Delia platura), Hessia fly (Mayetiola destructor),melon fly (Dacus (Zengodacus) cucurbitae), Mediterranear fruit fly(Ceratitis capitata), house flies (Musca domestica), stable fly(Stomoxys calcitrans), sheep ked (Melophagus orinus), common cattle grub(Hypoderm lineatum), nothern cattle grub (Hypoderma boris), sheep boffly(Oestrus ovis), tsetse fly (Golossina palpais), Prosimulium yezoensis,Tabanus trigonus, bath room fly (Telmatoscopus albipunctatus),Leptoconops nipponensis, common gnat (Culex pipiens pallens),yellow-fever mosquitoes (Aedes aegypti), Aëdes albopictus, Anophelesculicifacies, etc.;

Insect pests of Hymenoptera, such as cabbage sawfly (Athalis rosaeruficornis), pine sawfly (Neodiprion sertifer), chestnut sawfly(Apethymust kuri), soldier ant, Camponotus japonicus, giant hornet(Vespa mandarina), bulldog ant, fire ant, pharaoh ant, etc.;

Insect pests of Thysanoptera, such as melon thrips (Thrips palmi), onionthrips (Thrips tabaci), western flower thrips (Frankliniellaoccidentalis), flower thrips (Frankliniella intonsa), yellow tea thrip(Scirtothrips dorsalis), etc.; Insect pests of Dictyoptera, such assmokybrown cockroach (Periplaneta fuliginosa), Japanese cockroach(Periplaneta japonica), German cockroach (Blattella germanica), etc.;

Insect pests of Orthoptera, such as African mole cricket (Gryllotalpaafricana), field cricket (Teleogryllus emma), oriental migratory locust(Locusta migratoria), rice grasshopper (Oxya yezoensis), desert locust(Schistocerca gregaria), etc.; Insect pests of Isoptera, such asFormosan subterranean termit (Coptotermes formosanus), Reticulitermes(Leucotermes) speratus, Odontotermes formosanus, etc.;

Insect pests of Siphonaptera, such as fleas (Ctenocephalides felis),human fleas (Pulex irritans), oriental rat flea (Xenopsylla cheopis),etc.;

Insect pestd of Mallophaga, such as Chicken bodylouse (Menacanthusstramineus), cattle biting louse (Bovicola bovis), etc.;

Insect of pests of Anoplura, such as short-nosed cattle louse(Haematopinus eurystemus), hog louse (Haematopinus suis), long-nosedcattle louse (Linognathus vituli), little cattle louse (Solenopotescapillatus), etc.;

Pests of THYSANURA, such as oriental siverfish (Ctenolepisma villosa),etc.,;

Pests of PSOCOPTERA, such as Liposcelis bostrychophilus, etc.;

Pests of COLLEMBOLA, such as Onychiuras pseudarmatus yagii,ONYCHIURIDAE, etc.,;

Pests of TETRANYCHIDAE, such as citrus red mite (Panonychus citn),European red mite (Panonychus ulmi), two-spotted spider mite(Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawal), etc.;

ests of ERIOPHYDAE, such as pink citrus rust mite (Aculops pelekassi),pear rust mite (Epitrimerus pyri), dry bulb mite (Aceria tulipae), pinktea mite (Acaphylla theae), etc.;

Pests of TARSONEMIDAE, such as broad mites (Polyphagotarsonemus latus),cyclamen mite, strawberry mite (Steneotarsonemus pallidus), etc.;

Pests of ACARIDAE, such as mold mite, copra mite, forage mite(Tyrophagus putrescetiae), bulb mite (Rhizoglyphus robini), etc.;

Pests of VARROIDAE, such as bee brood mite (Varroa jacobsoni), etc.;

Pests of Ixodide, such as bull ticks (Boophilus mivroplus),Haemaphysalis Iongicornis, etc.;

Pests of Sarcoptidae, such as sarcoptes mange mite (Sarcaptes scabieiLinné), etc.

Pests of Chilopodera, such as Sclopendra subspinipes japonica,Thereuronema hilgendorfi, etc.,;

Pests of Diplopoda, such as hot house millipede (Oxidus gracilis),etc.,;

Nematodes, such as southern root-knot nematodae (Meloidogyne incognita),northern root-knot nematodae (Meloidogyne hapla), Cobb root-lesionnematode (Pratylenchus penetraus), walnut root-lesion nematode(Pratylenchus vulnus), potato cyst nematode (Globodera rostochiensis),pine wood nematode (Bursaphelenchus xylophilus), etc.;

Mollusca, such as apple snali (Pomacea canaliculta), Incilariapilineata, giant African snail (Achatina fulica), Acusta despectasieboldiana, Euhadra peliomphala, pillbug (Armadilliduim vulgara), etc.;

Crustaceans, such as pilibug (Armadilliduim vulgara), etc.

That is, the compounds of the present invention can effectively preventinsect pests including Orthoptera, Hemiptera, Lepidoptera, Coleoptera,Hymenoptera, Diptera and Isoptera as well as acari and lice, and diseasedamage to plants at low concentration. On the other hand, the compoundsof the present invention include very useful compounds that have littleadverse effect on mammals, fishes, crustaceans and beneficial insects.

The compounds (1) of the present invention can be produced according tothe following methods indicated in Scheme 1. That is, the compounds (1)of the present invention can be produced by reacting acyanomethyltriazole derivative of general formula (2) with a carboxylicacid derivative of general formula (3) in the presence of a base topartially give the aimed compounds, then the resulting compound isreacted with a compound of general formula (4) to obtain the compound ofpresent invention. The compounds of general formula (4) are concretelyacyl halides, benzoyl halides, alkyl halides, benzyl halides,alkoxyalkyl halides, alkoxyalkoxyalkyl halides, phenoxyalkyl halides,benzyloxyalkyl halides, alkylsulfonates, benzene sulfonates, toluenesulfonates, α-haloketones and α-haloesters, and the like.

[In Scheme 1, R, R¹, A and B have the same meanings as defined above; L¹and L² are a suitable leaving group, such as a chlorine atom, a bromineatom, an iodine atom, a C₁-C₄ alkylsulfonyloxy, a benzenesulfonyloxy, atoluenesulfonyloxy, 1-imidazolyl or 1-pyrazolyl.]

In some cases of the above-mentioned methods, it is preferable to use abase. The base includes, for example, alkali metal alkoxides such assodium ethoxide, sodium methoxide, potassium t-butoxide, etc., alkalimetal hydroxides such as sodium hydroxide, potassium hydroxide, etc.,alkali metal carbonates such as sodium carbonate, potassium carbonate,etc., organic bases such as triethylamine, pyridine, DBU, etc., organiclithium compounds such as butyl lithium, etc., lithium amides such aslithium diisopropylamide, lithium bistrimethylsilylamide, etc., andsodium hydride, and so on.

The reactions described above may be effected in a solvent that is inertto the reaction. The solvent includes, for example, lower alcohols suchas methanol, ethanol, etc., aromatic hydrocarbons such as benzene,toluene, etc., ethers such as diethyl ether, tetrahydrofuran,1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethane, etc., ketones suchas acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.,halogenated hydrocarbons such as methylene chloride, chloroform,1,2-dichloroethane, etc., amides such as dimethylformamide,dimethylacetamide, 1,3-dimethylimidazolidinone, etc., nitrites such asacetonitrile, etc., dimethylsulfoxide, and mixed solvents of these. Asthe case may be, a quaternary ammonium salt such astetra-n-butylammonium bromide may be added to the reaction system as acatalyst to obtain good results. The reaction temperature may be freelysettled within a range between −70° C. and 200° C. When the reactiontemperature falls between 0° C. and 150° C. or a solvent is used, thetemperature preferably ranges from −70° C. to the boiling point of thesolvent. The base may be used in an amount of from 0.05 to 10equivalents, preferably from 0.05 to 3 equivalents, of the reactionsubstrate.

The cyanomethyltriazole derivatives of general formula (2) may besynthesized according to a method such as the method of Scheme 2.

[In Scheme 2, R and R¹ have the same meanings as defined above; R² is alower alkyl.]

The compounds of the present invention may be obtained from reactionmixtures according to any ordinary methods. If the purification of thecompounds of the invention is needed, they can be separated and purifiedby any ordinary methods of, for example, recrystallization or columnchromatography.

Of the compounds of the invention, those having an asymmetric carbonatom include optically active compounds of (+) form and (−) form.

Examples of the compounds of the present invention are shown in Tables 1and 2 below. The abbreviations in these tables are as follows: Me:methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pen:pentyl group, Hex: hexyl group, Hep: heptyl group, Oct: octyl group,Non: nonyl group, Dec: decyl group, Ph: phenyl group, n: normal, i: iso,sec: secondary, t: tertiary, c: cyclo.

TABLE 1

R R¹ B Y₁ Y₂ Me H H H H Et Me CH₂SMe Me H nPr Me SO₂NHMe H Me iPr MeSO₂NMe₂ Cl Cl nBu Me CSNHEt H CF₃ iBu Me CSNMe₂ Me MeO sBu Me CH₂COOEtMe CF₃O tBu Me COtBu H Me tBu Me COtBu Me H tBu Me COtBu Me Me tBu MeCOtBu Cl Me tBu Me COtBu Me Cl tBu Me COtBu Me Br tBu Me COtBu CF₃ MetBu Me COtBu F H tBu Me COtBu F F tBu Me COOMe Me Me tBu Me COOiBu Me MetBu Me CO(2-Cl—Ph) H Me tBu Me SO₂Ph Me Me tBu Me Me Cl Me tBu Me CH₂OEtCl Et tBu Et COtBu Me Et tBu nPr COtBu H Me tBu iPr COtBu Me Me tBu nBuCOtBu Cl Me tBu nPen COOMe Cl Et tBu nHex COOiBu Me Et tBu CNCO(2-Cl—Ph) H Me tBu COOMe SO₂Ph Me Me tBu OMe Me Cl Me tBu OnHex CH₂OEtCl Et nPen NO₂ COtBu Me Et nHex COMe COtBu H Me cPr Ph COtBu Me Me cPenCH₂Ph COtBu H Me cHex H COtBu Me Me cHex Me COtBu Cl Me cHex Me COtBu ClEt cHex H COtBu Me Et cHex Me Me Me H cHex Me CH₂OEt CF₃ Me cHep MeCOtBu Me Me cHep Me COtBu H Me cHep Me COtBu Cl Me cHep nBu H Me Me Ph HH CF₃ Me Ph H COtBu Me Me Ph H COtBu H Me Ph H COtBu Cl Me Ph H COtBu ClH Ph H COtBu F H Ph H COtBu F F Ph H COtBu Cl Et Ph Me COtBu Cl Et Ph MeCOtBu Cl nPr Ph Me COtBu Cl nBu Ph Me COtBu Me Et Ph Me COtBu Me CF₃ PhMe COtBu Cl Cl Ph Me COtBu Cl H Ph Me COtBu Br H Ph Me COtBu Me H Ph MeCOtBu Me Br Ph Me COtBu Me Cl Ph Me COMe H Me Ph Me COCH═CH₂ Me Me Ph MeCOCH═CMe₂ Cl Me Ph Me COCF₃ Cl Et Ph Me COCF₂CF₃ Me Et Ph Me COCH₂OMe MeH Ph Me CO(2,2-F₂-cPr) CF₃ Me Ph Me COOCH₂CH₂Cl H Me Ph Me COOCH₂CMe═CH₂Me Me Ph Me COcPr Cl Me Ph Me CO(1-Me-cPr) Cl Et Ph Me COcHex Me Et PhMe CO(1-Me-cHex) Me H Ph Me COOcPen CF₃ Me Ph Me COOCH₂Ph H Me Ph MeCOCOOMe Me Me Ph Me CONHMe Cl Me Ph Me CONHPh Cl Et Ph Me CON(COMe)Me MeEt Ph Me CON(COOMe)Et Me H Ph Me CONMe₂ CF₃ Me Ph Me CONMePh H Me Ph MeCONMeCH₂Ph Me Me Ph Me COPh Cl Me Ph Me CO(2-Cl—Ph) Cl Et Ph MeCO(2-Me—Ph) Me Et Ph Me CO(2-CF₃—Ph) Me H Ph Me CO(2-MeO—Ph) CF₃ Me PhMe CO(2-CHF₂O—Ph) H Me Ph Me CO(2-MeS—Ph) Me Me Ph Me CO(2-MeSO—Ph) CF₃SMe Ph Me CO(2-MeSO₂Ph) CF₃SO Et Ph Me CO(2-CF₃S—Ph) CF₃SO₂ Et Ph MeCO(2-CBrF₂SO—Ph) Me H Ph Me CO(2-CHF₂SO₂—Ph) CF₃ Me Ph Me CO(3-NO₂—Ph) HMe Ph Me CO(4-CN—Ph) Me Me Ph Me CO(4-NMe₂—Ph) Cl Me Ph Me CO(2,6-F₂—Ph)Cl Et Ph Me CO(2,6-Cl₂—Ph) Me Et Ph Me CO(3,4-(MeO)₂—Ph) Me H Ph MeCO(2,4,6-Me₃—Ph) CF₃ Me Ph Me CO(1-naphthyl) H Me Ph Me CO(2-pyridinyl)Me Me Ph Me CO(3-pyridinyl) Cl Me Ph Me CO(4-pyridinyl) Cl Et Ph EtCO(2,6-F₂—Ph) H Me Ph Et COtBu Cl Et Ph Et COtBu Cl H Ph Et COtBu Br HPh Et COtBu NO₂ Me Ph nPr COtBu Me Me Ph iPr COtBu Cl Me Ph nBu COtBu ClEt Ph iBu COtBu CF₃ Me Ph sBu COtBu Me H Ph nPen COtBu Me Br Ph nHexCOtBu Cl Et Ph CN COtBu Me Me Ph CO₂Me COtBu Cl Me Ph CO₂Et COtBu Cl EtPh CO₂nPr COtBu CF₃ Me Ph CO₂nBu COtBu Me H Ph CO₂nPen COtBu Me Br PhCO₂nHex COtBu H Me Ph CONH₂ COtBu Me Me Ph CONHMe COtBu Cl Me Ph CONHEtCOtBu Cl Et Ph CONHnPr COtBu CF₃ Me Ph CONHiPr COtBu Me H Ph CONHnBuCOtBu Me Br Ph CONHPh COtBu H Me Ph CONMe₂ COtBu Me Me Ph CONMeEt COtBuCl Me Ph CONEt₂ COtBu Cl Et Ph CONMePh COtBu CF₃ Me Ph CONEtPh COtBu MeH Ph CONMe(2-Cl—Ph) COtBu Me Br Ph CONMe(4-CF₃—Ph) COtBu H Me PhCONMe(3-Me—Ph) COtBu Me Me Ph CONEt(3,4-(MeO)₂Ph) COtBu Cl Me Ph OMeCOtBu Cl Et Ph OEt COtBu CF₃ Me Ph OnPr COtBu Me H Ph OiPo COtBu Me BrPh OnBu COtBu H Me Ph OiBu COtBu Me Me Ph OsBu COtBu Cl Me Ph OtBu COtBuCl Et Ph OnPen COtBu CF₃ Me Ph OCH₂tBu COtBu Me H Ph OnHex COtBu Me BrPh CH₂OMe COtBu H Me Ph CH₂OnPr COtBu Cl Me Ph CH₂OiPr COtBu Cl Et PhCH₂OnBu COtBu CF₃ Me Ph CH₂OnPen COtBu Me H Ph CH₂SMe COtBu Me Br PhCH₂SEt COtBu H Me Ph CH₂SnPr COtBu Me Me Ph CH₂SiPr COtBu Cl Me PhCH₂SnBu COtBu Cl Et Ph CH₂SiBu COtBu CF₃ Me Ph CH₂SnPen COtBu Me H Ph ClCH₂OC₂H₄OMe Me Br Ph Br CH₂Ph H Me Ph I C₂H₄Ph Me Me Ph CF₃ CH₂COPh ClMe Ph CClF₂ SiMe₃ Cl Et Ph CF₂CF₃ SO₂Me CF₃ Me Ph Me PO(OMe)₂ Me H Ph MePS(OEt)₂ Me Br Ph Me Na H Me Ph Me K Me Me Ph Me NHEt₃ Cl Me Ph MeNH(—(CH₂)₄—) Cl Et Ph Me NH(—(CH₂)₅—) CF₃ Me Ph Me NH(—(CH₂)₆—) Me Me PhMe NH(—(CH₂)₇—) Me Me Ph Me NH(—CH₂H₄OC₂H₄—) H Me 2-F—Ph H COtBu Me H2-F—Ph Me COtBu Me Br 2-F—Ph Me COtBu H Me 2-F—Ph Me COtBu Me Me 2-F—PhMe COtBu Cl Me 2-F—Ph Me COtBu Cl Et 2-F—Ph Me COtBu CF₃ Me 2-F—Ph H HMe Me 2-F—Ph Me H Me Me 2-Cl—Ph H COtBu Me H 2-Cl—Ph Me COtBu Me Br2-Cl—Ph Me COtBu H Me 2-Cl—Ph Me COtBu Me Me 2-Cl—Ph Me COtBu Cl Me2-Cl—Ph Me COtBu Cl Et 2-Cl—Ph Me COtBu CF₃ Me 2-Cl—Ph Et COtBu Me Me2-Cl—Ph CO₂Me COtBu Me Me 2-Br—Ph H COtBu Me H 2-Br—Ph Me COtBu Me Br2-Br—Ph Me COtBu H Me 2-Br—Ph Me COtBu Me Me 2-Br—Ph Me COtBu Cl Me2-Br—Ph Me COtBu Cl Et 2-Br—Ph Me COtBu CF₃ Me 2-Me—Ph Me COtBu Me H2-Et—Ph Me COtBu Me Br 2-CF₃—Ph Me COtBu H Me 2-MeO—Ph Me COtBu Me Me2-CHF₂O—Ph Me COtBu Cl Me 2-MeS—Ph Me COtBu Cl Et 2-EtSO—Ph Me COtBu CF₃Me 2-nPrSO₂—Ph Me COtBu Me H 2-CF₃S—Ph Me COtBu Me Br 2-CF₃SO—Ph MeCOtBu H Me 2-CF₃SO₂—Ph Me COtBu Me Me 2-NO₂—Ph Me COtBu Cl Me 2-CN—Ph MeCOtBu Cl Et 2-Ph—Ph Me COtBu CF₃ Me 2-PhO—Ph Me COtBu Me Me 2,3-Cl₂—Ph HCOtBu Me H 2,6-F₂—Ph Me COtBu Me Br 2,6-F₂—Ph Me COtBu H Me 2,6-F₂—Ph MeCOtBu Me Me 2,6-F₂—Ph Me COtBu Cl Me 2,6-F₂—Ph Me COtBu Cl Et 2,6-F₂—PhMe COtBu CF₃ Me 2,6-F₂—Ph Me CO₂Me Me H 2,6-F₂—Ph Et Me H Me 2,6-F₂—PhCN CO(2-Cl—Ph) Cl Me 2,6-F₂—Ph CO₂Et COcHex Me Me 2,6-F₂—Ph OnBu SO₂CF₃H Me 2,6-Cl₂-4-CF₃—Ph Me COtBu Me Me 1-naphthyl H COtBu CF₃ Me2-naphthyl Br COtBu Me H 2-pyridyl CF₃ COtBu H Me 3-pyridyl COOnPenCOtBu Cl Me 4-pyridyl COMe COtBu Me Me 2-pyridyl H H Me Me 2-pyridyl HCOtBu Me Me 2-pyridyl Me H Me Me 2-pyridyl Me COtBu Me Me 2-pyridyl iPrH Me Me 2-pyridyl iPr COtBu Me Me Ph CH₂OEt H Me Me Ph CH₂OEt COtBu MeMe Ph CH₂OnPr H Me Me Ph CH₂OnPr COtBu Me Me Ph CH₂OiPr H Me Me PhCH₂OiPr COtBu Me Me Ph CH₂OnBu H Me Me Ph CH₂OnBu COtBu Me Me Ph CH₂OPhH Me Me Ph CH₂OPh COtBu Me Me

TABLE 2

R R¹ B A Y₁ Y₃ Ph Me H A-9 3-Cl — Ph Me COtBu A-9 3-Cl — Ph Me COtBu A-93-Me — Ph Me COtBu A-9 3,4-Cl₂ — Ph Et COtBu A-10 4-OMe — Ph Et COtBuA-10 4-OMe-5-Cl — Ph Me COtBu A-11 3-Cl — Ph Me COtBu A-12 4-Cl — tBu HCOtBu A-13 2-Cl — Ph Me COtBu A-14 3-Me Me Ph iPr COtBu A-15 2-Me Me PhMe COtBu A-16 4-Me — Ph Me COtBu A-17 2-Cl — Ph Me COtBu A-18 4-Me — PhMe COtBu A-19 2-Cl — Ph Me COtBu A-20 — — Ph Me COtBu A-21 4-Me Me Ph MeCOtBu A-22 2-Me Me Ph Me COtBu A-23 4-Me — Ph Me COtBu A-24 3-Me-4-Cl —Ph Et COtBu A-25 4-Cl — Ph Et COtBu A-26 3-Me-4-Cl — Ph nHex COtBu A-273,5-Me₂ — Ph CN COtBu A-28 Me — Ph CO₂Me COtBu A-29 Me — Ph OMe COtBuA-30 Me — Ph OnHex COtBu A-31 Me — Ph NO₂ COtBu A-32 Me — Ph COMe COtBuA-33 Me — Ph Me COtBu A-34 3,5-Me₂ — Ph Me COtBu A-35 5-Me Me Ph MeCOtBu A-36 3-Me Me Ph Et COtBu A-36 3-Me Me Ph Me COtBu A-37 Me Me Ph MeCOtBu A-38 3-Me — Ph Me COtBu A-39 Me — Ph Me COtBu A-40 Me — Ph MeCOtBu A-41 5-Me — Ph Me COtBu A-42 5-Me — Ph Me COtBu A-43 Me Me Ph MeCOtBu A-44 Me Me Ph Me COtBu A-45 Me Me Ph Me COtBu A-46 Me — Ph MeCOtBu A-47 Me — Ph Me COtBu A-48 — Me Ph Me COtBu A-49 — Me Ph Me COtBuA-50 — — Ph Me COtBu A-51 5-CF₃ — Ph Me COtBu A-52 4-CF₃ — Ph Me COtBuA-53 3-Me — Ph Me COtBu A-54 4-Me — Ph Me COtBu A-55 3-Me — Ph Me COtBuA-56 4-Me — Ph Me COtBu A-57 5-Me — Ph Me COtBu A-58 3-Me — Ph Me COtBuA-59 4-Me — Ph Me COtBu A-60 3,5-Me₂ — Ph Me COtBu A-61 4-Cl Me Ph MeCOtBu A-62 3-Me Me Ph Me COtBu A-63 3-Me Me Ph Me COtBu A-64 2-Cl — PhMe COtBu A-65 3-Me Me Ph Me COtBu A-66 2,4-Me₂ Me Ph Me COtBu A-672,5-Me₂ Me Ph Me COtBu A-68 4-Me Me Ph Me COtBu A-69 Me — Ph Me COtBuA-70 Me — Ph Me COtBu A-71 Me — Ph Me COtBu A-72 Me — Ph Me COtBu A-73(2-yl) 4-Me — Ph Me COtBu A-74 (2-yl) 4-Me — Ph Me COtBu A-75 (2-yl)4-Me Me Ph Me COtBu A-76 (2-yl) 4-Me — Ph Me COtBu A-77 (2-yl) 4-Me — PhMe COtBu A-78 (2-yl) 4-Me Me Ph Me COtBu A-79 (3-yl) 4-Me — Ph Me COtBuA-80 (3-yl) 4-Me Me Ph Me COtBu A-81 (3-yl) 4-Me Me Ph Me COtBu A-82(3-yl) 4-Me — Ph Me COtBu A-83 (3-yl) 4-Me Me Ph Me COtBu A-84 (3-yl)4-Me Me Ph Me COtBu A-85 (2-yl) 4,5-Cl₂ — Ph Me COtBu A-86 (4-yl) 5-ClMe Ph Me COtBu A-87 4-Me — Ph Me COtBu A-88 (6-yl) 2-Me — Ph Me COtBuA-89 4-Me — Ph Me COtBu A-90 (6-yl) 2-Me — Ph Me COtBu A-91 2-Me — Ph MeCOtBu A-92 — Me Ph Me COtBu A-93 (5-yl) 6-NO₂ Me Ph Me COtBu A-94 3-Me —Ph Me COtBu A-95 — Me Ph Me COtBu A-96 — Me Ph Me COtBu A-97 (4-yl) 3-MeMe Ph Me COtBu A-98 (2-yl) 3-Me — Ph Me COtBu A-99 (4-yl) — — Ph MeCOtBu A-100 (2-yl) 3-Me — Ph Me COtBu A-101 (4-yl) — — Ph Me COtBu A-102— — Ph Me COtBu A-103 (3-yl) — Me Ph Me COtBu A-104 (4-yl) — Me Ph MeCOtBu A-105 — — Ph Me COtBu A-106 (3-yl) — — Ph Me COtBu A-107 — — Ph MeCOtBu A-108 (3-yl) — — Ph Me COtBu A-109 — — Ph Me COtBu A-110 (4-yl)3-Me — Ph Me COtBu A-111 — — Ph Me COtBu A-112 (4-yl) 3-Me — Ph Me COtBuA-113 — — Ph Me COtBu A-114 (3-yl) — — Ph Me COtBu A-115 — — Ph Me COtBuA-116 (3-yl) — — Ph Me COtBu A-117 (4-yl) — — Ph Me COtBu A-118 (4-yl) —— Ph Me COtBu A-119 — — Ph Me COtBu A-120 (4-yl) — Me Ph Me COtBu A-121— — Ph Me COtBu A-122 (7-yl) — Me Ph Me COtBu A-123 (4-yl) — — Ph MeCOtBu A-124 (8-yl) — — Ph Me COtBu A-125 (4-yl) — — Ph Me COtBu A-126(8-yl) — — Ph Me COtBu A-127 (4-yl) — — Ph Me COtBu A-128 (8-yl) — — PhMe COtBu A-129 (4-yl) — — Ph Me COtBu A-130 (8-yl) — — Ph Me COtBu A-131(2-yl) — — Ph Me COtBu A-132 (8-yl) — — Ph Me COtBu A-133 — — Ph MeCOtBu A-134 (8-yl) — — Ph Me COtBu A-135 (4-yl) — — Ph Me COtBu A-136(8-yl) — — Ph Me COtBu A-137 (4-yl) — — Ph Me COtBu A-138 (8-yl) — — PhMe COtBu A-139 (4-yl) — — Ph Me COtBu A-140 (8-yl) — — Ph Me COtBu A-141(4-yl) — — Ph Me COtBu A-142 (8-yl) — — Ph Me COtBu A-143 (4-yl) — — PhMe COtBu A-144 (6-yl) — — Ph Me COtBu A-145 — — Ph Me COtBu A-146 — MePh Me COtBu A-147 (2-yl) — Me Ph Me COtBu A-148 (7-yl) — — Ph Me COtBuA-149 (2-yl) — — Ph Me COtBu A-150 (7-yl) — — Ph Me COtBu A-151 (2-yl) ——

Where the compounds of the present invention are used as pesticides, ingeneral, they can be mixed with a suitable solid carrier or liquidcarrier, optionally along with surfactant, penetrating agent, spreadingagent, thickner, anti-freezing agent, binder, anti-caking agent, slidingagent, stabilizer, and the like, and can be formulated into any desiredforms for practical use, such as soluble concentrates, emulsifiableconcentrates, wettable powders, water soluble powders, water dispersiblegranules, water soluble granules, suspension concentrates, concentratedemulsions, suspoemulsions, microemulsions, dustable powders, granulesand gels. From the viewpoint of an elimination or reduction of labor andan improvement of safety, the formulations in any desired formsdescribed above may be included into a water soluble bag.

The solid carrier includes, for example, natural minerals such asquartz, kaolinite, pyrofilite, Celicite, talc, bentonite, acid clay,attapulgite, zeolite and diatomaceous earth, inorganic salts such ascalcium carbonate, ammonium sulfate, sodium sulfate and potassiumchloride, synthetic silicic acids and synthetic silicates.

The liquid carrier includes, for example, alcohols such as ethyleneglycol, propylene glycol and isopropanol, aromatic hydrocarbons such asxylene, alkylbenzene and alkylnaphthalene, ethers such asbutylcellosolb, ketones such as cyclohexanone, esters such asr-butyrolactone, amides such as N-methylpyrrolidone, N-octylpyrrolidone,vegetable oil such as soybean oil, rapeseed oil, cottonseed oil andcastor oil, and water.

These solid and liquid carriers may be used alone, or in a mixture oftwo or more carriers.

The surfactants includes, for example, nonionic surfactants such aspolyoxyethylene alkylether, polyoxyethylene alkylarylether,polyoxyethylene styrylphenylether, polyoxyethylene polyoxypropyleneblock copolymer, polyoxyethylene fatty ester, sorbitan fatty ester andpolyoxyethylene sorbitan fatty ester; anionic surfactants such as alkylsulfate, alkylbenzene sulfonate, lignin sulfonate, alkylsulfo succinate,naphthalene sulfonate, alkylnaphthalene sulfonate, a salt of condensateof naphthalene sulfonate with formalin, a salt of condensate ofalkylnaphthalene sulfonate with formalin, polyoxyethylene alkylarylethersulfate and phosphate, polyoxyethylene styrylphenylether sulfate andphosphate, polycarboxylate and polystyrene sulfonate; cationicsurfactants such as a salt of alkylamine and alkyl quaternary ammoniumsalt, and amphoteric surfactants such as amino acid type and betainetype.

The amount of the surfactant is not particularly limited, but ingeneral, is 0.05 to 20 parts by weight based on 100 parts by weight ofthe formulation of the present invention. In addition, these surfactantsmay be used alone or in a mixture of two or more surfactants.

In case where the compounds of the present invention are used asagricultural chemicals, they can be combined with any other herbicides,various insecticides, acaricides, nematocides, fungicides, plant growthregulators, synergists, fertilizer and soil improvers, when they areformulated into preparations for practical use or while they areactually used through spraying or the like.

In particular, the combination of the compounds of the invention andother agricultural chemicals or plant hormones will be advantageous inthat the amount of the chemicals to be used can be reduced therebyresulting in the reduction of the costs for the treatment, and that themixed chemicals exhibit synergistic effects to broaden the insecticidalspectrum while displaying higher pesticidal activities. If desired, thecompounds of the invention can be combined with a plurality of knownagricultural chemicals. For the agricultural chemicals capable of beingcombined with the compounds of the invention, for example, the compoundsdescribed in Farm Chemicals Handbook, 1994 are referred. Concretely, thegeneral names thereof are as follows, to which the present invention arenot limited.

Fungicides: acibenzolar-S-methyl, acylaminobenzamide, amobam,ampropyfos, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil,benomyl, benthiazole, benzamacril, binapacryl, biphenyl, bitertanol,bethoxazine, bordeaux mixture, blasticidin-S, bromoconazole, bupirimate,buthiobate, calcium polysulfide, captafol, captan, copper oxychloride,carpropamid, carbendazim, carboxin, CGA-279202, chinomethionat,chlobenthiazone, chlorfenazol, chloroneb, chlorothalonil, chlozolinate,cufraneb, cymoxanil, cyproconazol, cyprodinil, cyprofuram, dazomet,debacarb, dichlorophen, diclobutrazol, dichlofluanid, dichlomedine,dicloran, diethofencarb, dichlocymet, difenoconazole, diflumetorim,dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap,diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine,drazoxolon, edifenphos, epoxiconazole, etaconazole, ethirimol,etridiazole, famoxadone, fenarimol, febuconazole, fenamidone,fendazosulam, fenfuram, fenhexamid, fenpiclonil, fenpropidin,fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil,fluoroimide, fluquinconazole, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl,furametpyr, guazatine, hexachlorobenzene, hexaconazole, hymexazol,imazalil, imibenconazole, iminoctadine, ipconazole, iprobenfos,iprodion, isoprothiolane, iprovalicarb, kasugamycin, kresoxim-methyl,mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl,metconazole, methasulfocarb, metiram, metominostrobin, myclobutanil,MTF-753, nabam, nickel bis(dimethyldithiocarbamate),nitrothal-isopropyl, nuarimol, NNF-9425, octhilinone, ofurace, oxadixyl,oxycarboxin, oxopoconazole fumarate, pefurzoate, penconazole,pencycuron, phthalide, piperalin, polyoxins, potassium hydrogencarbonate, probenazole, prochloraz, procymidone, propamocarbhydrochloride, propiconazole, propineb, pyrazophos, pyrifenox,pyrimethanil, pyroquilon, quinomethionate, quinoxyfen, quintozene,RH7281, sodium hydrogen carbonate, sodium hypochlorite, sulfur,spiroxamine, tebuconazole, tecnazene, tetraconazole, thiabendazole,thiadiazin/milneb, thifluzamide, thiophanate-methyl, thiram,tolclofos-methyl, tolylfluanid, triadimefon, toriadimenol, triazoxide,tricyclazole, tridemorph, triflumizole, triforine, triticonazole,validamycin, vinclozolin, zinc sulfate, zineb, ziram and an extract frommycelium of shiitake (Cortinellus shiitake);

Bactriocides: strptomycin, tecloftalam, oxyterracycline and oxolinicacid;

Nematocides: aldoxycarb, cadusafos, fosthiazate, fosthietan, oxamyl andfenamiphos;

Acaricides: acequinocyl, amitraz, bifenazate, bromopropylate,chinomethionat, chlorobenzilate, clofentezine, cyhexatine, dicofol,dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin,fenproximate, halfenprox, hexythiazox, milbemectin, propargite,pyridaben, pyrimidifen and tebufenpyrad;

Insecticides: abamectin, acephate, acetamipirid, aldicarb, allethrin,azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin,buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap,chlorofenapyr, chlorpyrifos, chlorfenvinphos, chlorfluazuron,clothianidin, chromafenozide, chlorpyrifos-methyl, cycloprothrin,cyfluthrin, beta-cyfluthrin, cypermethrin, cyromazine, cyhalothrin,lamda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diacloden,diflubenzuron, dimethylvinphos, diofenolan, disulfoton, dimethoate,emamectin-benzoate, EPN, esfenvalerate, ethiofencarb, ethiprole,etofenprox, etrimfos, fenitrothion, fenobucarb, fenoxycarb,fenpropathrin, fenvalerate, fipronil, fluacrypyrim, flucythrinate,flufenoxuron, flufenprox, tau-fluvalinate, fonophos, formetanate,formothin, furathiocarb, halofenozide, hexaflumuron, hydramethyinon,imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion, lufenuron,malathion, metaldehyde, methamidophos, methidathion, methacrifos,metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide,monocrotophos, muscalure, nidinotefuran, nitenpyram, omethoate,oxydemeton-methyl, oxamyl, parathion, parathion-methyl, permethrin,phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon,pirimicarb, pirimiphos-methyl, profenofos, protrifenbute, pymetrozine,pyraclofos, pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad,sulfotep, tebfenozide, teflubenzuron, tefluthorin, terbufos,tetrachlorvinphos, thiacloprid, thiocyclam, thiodicarb, thiamethoxam,thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron,triflumuron and vamidothion.

The dose of the compounds of the present invention varies depending onan applicaction place, an application time, an application method,cultivation crops, etc. In general, it may be between approximately0.005 kg and 50 kg per hectare (ha) in terms of the amount of the activeingredient.

BEST MODE FOR CARRYING OUT THE INVENTION

Now, formulation examples comprising the compounds of the invention arementioned below, to which the invention is not limited. In the followingformulation examples, “part” or “parts” are by weight.

[Wettable Powders]

Compound of the invention 0.1 to 80 parts Solid carrier 5 to 98.9 partsSurfactant 1 to 10 parts Others 0 to 5 parts

The others include, for example, anti-caking agent, stabilizer, etc.

[Emulsifiable Concentrates]

Compound of the invention 0.1 to 30 parts Liquid carrier  45 to 95 partsSurfactant 4.9 to 15 parts Others   0 to 10 parts

The others include, for example, spreading agent, stabilizer, etc.

[Suspension Concentrates]

Compound of the invention 0.1 to 70 parts Liquid carrier 15 to 98.89parts Surfactant 1 to 12 parts Others 0.01 to 30 parts

The others include, for example, anti-freezing agent, thickener, etc.

[Water Dispersible Granules]

Compound of the invention 0.1 to 90 parts Solid carrier 0 to 98.9 partsSurfactant 1 to 20 parts Others 0 to 10 parts

The others include, for example, binder, stabilizer, etc.

[Soluble Concentrates]

Compound of the invention 0.01 to 70 parts Liquid carrier 20 to 99.99parts Others 0 to 10 parts

The others include, for example, anti-freezing agent, spreading agent,etc.

[Granules]

Compound of the invention 0.01 to 80 parts Solid carrier 10 to 99.99parts Others 0 to 10 parts

The others include, for example, binder, stabilizer, etc.

[Dustable Powders]

Compound of the invention 0.01 to 30 parts Solid carrier 65 to 99.99parts Others 0 to 5 parts

The others include, for example, anti-drifting agent, stabilizer, etc.

FORMULATION EXAMPLES

Now, Formulation Examples of pesticides comprising the compounds of thepresent invention as an active ingredient are shown below, which,however, are not intended to restrict the scope of the presentinvention. In the following Formulation Examples, “part” or “parts” areby weight.

FORMULATION EXAMPLE 1 Wettable Powder

Compound No. 17 of the invention 20 parts Pyrrofilite 76 parts Solpol5039  2 parts (trade name, a mixture of non-ionic surfactant and anionicsurfactant, manufactured by Toho Chemical Co., Ltd.) Carplex #80D  2parts (trade name, a synthetic silicic acid hydrate manufactured byShionogi Pharmaceutical Co., Ltd.)

The above-mentioned components are homogeneously mixed and ground toform a wettable powder.

FORMULATION EXAMPLE 2 Emulsifiable Concentrate

Compound No. 17 of the invention  5 parts Xylene 75 partsN-methylpyrolidone 15 parts Solpol 2680  5 parts (trade name, a mixtureof non-ionic surfactant and anionic surfactant, manufactured by TohoChemical Co., Ltd.)

The above-mentioned components are homogeneously mixed to form anemulsifiable concentrate.

FORMULATION EXAMPLE 3 Suspension Concentrate (Flowable)

Compound No. 17 of the invention   25 parts Agrisol S-710   10 parts(trade name, non-ionic surfactant manufactured by Kao Corp.) Runox 1000C 0.5 parts (trade name, anionic surfactant manufactured by Toho ChemicalCo., Ltd.) Xanthane gum  0.2 parts Water 64.3 parts

The above-mentioned components are homogeneously mixed and ground in wetto form a suspension concentrate.

FORMULATION EXAMPLE 4 Water Dispersible Granule (Dry Flowable)

Compound No. 17 of the invention 75 parts Hitenol NE-15  5 parts (tradename, anionic surfactant manufactured by Daiichi IndustrialPharmaceutical Co. Ltd.) Vanilex N 10 parts (trade name, anionicsurfactant manufactured by Japan Paper-manufacturing Co., Ltd.) Carplex#80D 10 parts (trade name, a synthetic silicic acid hydrate manufacturedby Shionogi Pharmaceutical Co., Ltd.)

The above-mentioned components are homogeneously mixed and ground, thenmixed with stirring after adding a small amount of water, and aregranulated with an extrusion granulator, and dried into a waterdispersible granule.

FORMULATION EXAMPLE 5 Granule

Compound No. 17 of the invention  5 parts Bentonite 50 parts Talc 45parts

The above-mentioned components are homogeneously mixed and ground, thenmixed with stirring after adding a small amount of water, and aregranulated with an extrusion granulator, and dried into a granule.

FORMULATION EXAMPLE 6 Dustable Powder

Compound No. 17 of the invention   3 parts Carplex #80D 0.5 parts (tradename, a synthetic silicic acid hydrate manufactured by ShionogiPharmaceutical Co., Ltd.) Kaolinite  95 parts Diisopropyl phosphate 1.5parts

The above-mentioned components are homogeneously mixed and ground toform a dustable powder.

Upon use, the wettable powder, emulsifiable concentrate, flowable andwater dispersible granule are diluted from 50 to 20000 times with water,and applied in amount of from 0.005 to 50 kg/ha in terms of the activeingredient.

Now, Synthesis Examples and Test Examples of the compounds of thepresent invention are shown as Examples below, which, however, are notintended to restrict the scope of the invention.

REFERENCE EXAMPLE 1 Synthesis of Cyanomethyltriazole Derivative (AMethod)

A synthesis method of cyanomethyltriazole according to A methoddescribed above will be explained below. Novel compounds also areincluded in intermediates described below. In the physical propertiesindicated below, the unit of melting points is ° C. and the values ofNMR are chemical shifts in 1H-NMR(CDCl₃, ppm).

1) Synthesis of (1-aza-3-(Hydroxyimino)-2-methylbut-1-enyl)phenylamine

10 g of phenylhydrazine hydrochloride was dissolved in 100 ml ofethanol, and 6.8 g of sodium acetate was added thereto under coolingwith ice. 7.0 g of diacetyl monoxime was added dropwise to the reactionsolution, then stirred for 1 hour at room temperature. After ethanol wasdistilled off, the residue was washed with water to obtain 12.0 g of theaimed compound.

2) Synthesis of 4,5-Dimethyl-2-phenyl-1,2,3-triazol-1-oxide

15.0 g of copper(II) sulfate (penta hydrate) dissolved in 60 ml of wateradded dropwise to 11.5 g of(1-aza-3-(hydroxyimino)-2-methylbut-1-enyl)phenylamine dissolved in 120ml of pyridine at room temperature. After stirring overnight at roomtemperature, concentrated hydrochloric acid was added to the stirredsolution under cooling with ice to make it acid, then extracted withchloroform. The organic phase was washed with water and a saturated saltsolution, then dried over anhydrous sodium sulfate. After the solventwas distilled off, the deposited crystals was washed with isopropylether to obtain 8.8 g of the aimed compound.

3) Synthesis of (5-Methyl-2-phenyl-1,2,3-triazol-4-yl)methan-1-ol

7.1 g of 4,5-dimethyl-2-phenyl-1,2,3-triazol-1-oxide was dissolved in 25ml of toluene, and heated to 80° C. 4.8 g of acetyl chloride dilutedwith 13 ml of toluene and 9.1 ml of triethylamine diluted with 13 ml oftoluene were simultaneouly added dropwise thereto, keeping thetemperature below 85° C. After stirring for 1 hour at 80° C., 2.5 ml ofacetyl chloride diluted with 5 ml of toluene and 4.5 ml of triethylaminediluted with 5 ml of toluene were simultaneously added. After stirringfor 1 hour at 80° C., the solution was left overnight at roomtemperature. 7 ml of 30% aqueous solution of sodium hydroxide was added,then toluene and triethylamine were distilled off under reducedpressure. 5 ml of ethanol and 30% aqueous solution of sodium hydroxidewere added, and refluxed with heating for 1 hour. After ethanol wasdistilled off under reduced pressure, 50 ml of 10% saline solution wasadded, and left for some time at room temperature. The depositedcrystals was dissolved in ethyl acetate, washed with water and asaturated salt solution, then dried over anhydrous sodium sulfate. Afterthe solvent was distilled off, the residue was purified through silicagel column chromatography (hexan/ethyl acetate=1/2), then washed withhexan/diisopropyl ether (=10/1) to obtain 5.7 g of the aimed compound.

4) Synthesis of 4-Chloromethyl-5-methyl-2-phenyl-1,2,3-triazol

5.0 g of (5-methyl-2-phenyl-1,2,3-triazol4-yl)methan-1-ol was dissolvedin 35 ml of dichloromethane, then 6.3 g of thionyl chloride was addeddropwise thereto under cooling with ice. After stirring for 1 hour atroom temperature, 100 ml of water was added. The resulting solution wasmade alkaline with 8 g of potassium carbonate, then extracted withchloroform. The organic phase was washed with water and a saturated saltsolution, then dried over anhydrous sodium sulfate. After the solventwas distilled off, 5.2 g of the aimed compound was obtained.

5) Synthesis of 2-(5-Methyl-2-phenyl-1,2,3-triazol4-yl)ethanenitrile

1.8 g of sodium cyanide was suspended in 30 ml of DMF, and 5.0 g of4-chloromethyl-5-methyl-2-phenyl-1,2,3-triazol was added under coolingwith ice. After stirring for 3 hours at room temperature, an aqueoussolution of sodium hydroxide was added to the reaction solution to makeit alkaline, and extracted with toluene. The organic phase was washedwith water and a saturated salt solution, then dried over anhydroussodium sulfate. After the solvent was distilled off, the depositedcrystals were washed with hexane to obtain 4.3 g of the aimed compound.

2-(5-ethyl-2-phenyl-1,2,3-triazol4-yl)ethanenitrile was synthesized in asimilar manner of 1) to 5) described above except that2-(hydroxyimino)pentane-3-on was used as a starting material.

REFERENCE EXAMPLE 2 Synthesis of Cyanomethyltriazole Derivative (BMethod)

A synthesis method of cyanomethyltriazole according to B methoddescribed above will be explained below. Novel compounds also areincluded in intermediates described below. In the physical propertiesindicated below, the units of melting points are ° C. and the values ofNMR are chemical shifts in 1H-NMR(CDCl₃, ppm).

1) Synthesis of Methyl-3-aza-3-(phenylamino)-2-propanoylprop-2-enoate

8.83 g of sodium nitrite dissolved in 25 ml of water was added dropwiseto 11.67 g of aniline dissolved in 130 ml of 2N hydrochloric acid at 0°C. 32.8 g of sodium acetate and the reaction solution comprisingdiazonium salt were simultaneously added to 16.25 g of methylpropionylacetate suspended in 100 ml of water at 21-23° C. The deposited solidwas filtrated out, and washed with water to obtain the aimed compound.

2) Synthesis of Ethyl-5-ethyl-2-phenyl-1,2,3-triazole-4-carboxylate

Hydroxylamine-O-sulfonic acid dissolved in 200 ml of water was addeddropwise at room temperature tomethyl-3-aza-3-(phenylamino)-2-propanoylprop-2-enoate synthesized in 1)dissolved in 300 ml of ethanol. After stirring overnight at roomtemperature, the reaction solution was neutralized with sodiumhydrogencarbonate, and stirred for 3 hours at room temperature. Ethanolwas distilled off under reduced pressure, and extracted with ethylacetate. The organic phase was washed with water, and dried overanhydrous sodium sulfate. After the solvent was distilled off, theresidue was purified through silica gel column chromatography(chloroform) to obtain 13.9 g of the aimed compound.

3) Synthesis of (5-Ethyl-2-phenyl-1,2,3-triazol-4-yl)methan-1-ol

11.55 g of ethyl-5-ethyl-2-phenyl-1,2,3-triazole-4-carboxylate dissolvedin a mixed solvent of 150 ml of ether and 30 ml of THF was addeddropwise at 3-8° C. to LiAIH₄ suspended in 100 ml of ether. Afterstirring overnight at room temperature, a small amount of saturatedsodium sulfate solution was added thereto. Insoluble materials werefiltered off, and the filtrate was dried over anhydrous sodium sulfate.The solvent was distilled off to obtain 9.40 g of the aimed compound.

(5-isopropyl-2-phenyl-1,2,3-triazol-4-yl)methan-1-ol was synthesized ina similar manner of 1) to 3) described above except that ethylisobutyrylacetate was used as a starting material.

Next, cyanomethyltriazole derivatives can be synthesized similarly toReference Example 1.

SYNTHESIS EXAMPLE 1 Synthesis of3-(2,4-Dimethylthiazol-5-yl)-3-hydroxy-2-(5-methyl-2-phenyl-1,2,3-triazol4-yl)acrylonitrile(Compound No. 20)

0.90 g of 4-cyanomethyl-5-methyl-2-phenyl-1,2,3-triazole and 1.04 g of1-(2,4-dimethylthiazol-5-carbonyl)pyrazole were dissolved intetrahydrofuran, and 1.02 g of potassium tert-butoxide was added theretoat 0° C. After stirring for 1 hour at room temperature, dilutedhydrochloric acid was added to the reaction solution to make it acid.The solution was extracted with ethyl acetate, and dried over anhydroussodium sulfate. The solvent was distilled off under reduced pressure,and the resulting solid was washed with isopropyl ether to obtain 0.79 gof the aimed compound. m.p.: 117-118° C.

SYNTHESIS EXAMPLE 2 Synthesis of3-(2,4-Dimethylthiazol-5-yl)-3-2-(5-methyl-2-phenyl-1,2,3-triazol-4-yl)acrylonitrile(Compound No. 20)

0.6 g of3-(2,4-dimethylthiazol-5-yl)-3-hydroxy-2-(5-methyl-2-phenyl-1,2,3-triazol-4-yl)acrylonitrilewas dissolved in chloroform, 0.22 g of triethylamine was added thereto,and 0.26 g of pivaloyl chloride was further added dropwise. Afterstirring for 3 hours at room temperature, the solution was washed withwater, dried over anhydrous sodium sulfate, and the solvent wasdistilled off under reduced pressure. The resulting crystals were washedwith a mixed solvent of hexane/isopropyl ether to obtain 0.59 g of theaimed compound (a mixture of E-form and Z-form). m.p.: 119-122° C.

In accordance with the above-mentioned reaction schemes or SynthesisExamples, various compounds of the present invention were produced, ofwhich the structure and the melting point are shown in Table 3 below.Unless otherwise specifically indicated, the compounds shown in thetable are in form of a mixture of E-form and Z-form. The abbreviationsin the table have the same meanings as those mentioned above.

TABLE 3

No. R R¹ B A Y₁ Y₂ Y₃ m.p. (° C.), ratio of isomers 1 2-Cl—Ph Me COtBuA-3 Me Me — 109.5-110, E-form or Z-form 2 2-Cl—Ph Me COtBu A-3 Me Me —resinous, Z-form or E-form 3 Ph Me H A-1 Me Me Me resinous 4 Ph Me COtBuA-1 Me Me Me 139-142, E-form or Z-form 5 Ph Me COtBu A-1 Me Me Me133-135, Z-form or E-form 6 Ph Me H A-1 Cl Me Me 140-141 7 Ph Me COtBuA-1 Cl Me Me 137-138, E-form or Z-form 8 Ph Me H A-1 H Me Me 118-119 9Ph Me COtBu A-1 H Me Me 104-108, E-form/Z-form mixture 10 Ph Me H A-1 MeH Me 140-141 11 Ph Me COtBu A-1 Me H Me 171-177, E-form/Z-form mixture12 Ph Me H A-1 Me Br Me 171-177 13 Ph Me COtBu A-1 Me Br Me 163-164,E-form or Z-form 14 2-Me—Ph Me H A-1 Me Me Me resinous 15 2-Me—Ph MeCOtBu A-1 Me Me Me resinous, E-form/Z-form mixture 16 2-F—Ph Me H A-1 MeMe Me 126-127 17 2-F—Ph Me COtBu A-1 Me Me Me 113-116, 3/2 18 2,6-Cl₂—PhMe H A-1 Me Me Me 203-204 19 2,6-Cl₂—Ph Me COtBu A-1 Me Me Me resinous,E-form/Z-form mixture 20 Ph Me H A-3 Me Me — 117-118 21 Ph Me COtBu A-3Me Me — 119-122, E-form/Z-form mixture 22 Ph Me H A-3 CF₃ Me — 143-14523 Ph Me COtBu A-3 CF₃ Me — 141-142, E-form or Z-form 24 Ph Me COPh A-3CF₃ Me — 115-118, E-form/Z-form mixture 25 Ph CN COtBu A-1 Me Me Meresinous, 5/4 26 Ph Me SO₂Me A-1 Me Me Me resinous, 5/4 27 Ph Me SO₂PhA-1 Me Me Me resinous, 4/1 28 Ph Me CO(2- A-1 Me Me Me resinous, 5/3Cl—Ph) 29 Ph Me CO₂iBu A-1 Me Me Me resinous, 2/1 30 Ph Me CH₂OEt A-1 MeMe Me resinous, 3/1 31 Ph Me Me A-1 Me Me Me resinous, 3/1 32 2-Cl—Ph MeH A-1 Me Me Me resinous 33 2-Cl—Ph Me COtBu A-1 Me Me Me resinous, 2/334 2-Br—Ph Me H A-1 Me Me Me resinous 35 2-Br—Ph Me COtBu A-1 Me Me Meresinous, 9/11 36 tBu Me H A-1 Me Me Me resinous 37 tBu Me COtBu A-1 MeMe Me resinous, E-form/Z-form mixture 38 Ph COOMe H A-1 Me Me Meresinous 39 Ph CONMe₂ COtBu A-1 Me Me Me resinous, 4/1 40 Ph CO(N- COtBuA-1 Me Me Me resinous, 6/1 piperidyl) 41 2-Me—Ph Me COtBu A-1 Cl Me Meresinous, 1/1 42 Ph CH₂SMe H A-1 Cl Me Me 104-106 43 Ph CH₂SMe COtBu A-1Cl Me Me resinous 44 Ph nBu H A-1 Cl Me Me 121-123 45 Ph nBu COtBu A-1Cl Me Me resinous, 1/1 46 Ph Et H A-1 Cl Me Me 125-127 47 Ph Et COtBuA-1 Cl Me Me resinous, 1/1 48 Ph nPr H A-1 Cl Me Me 91-93 49 Ph nPrCOtBu A-1 Cl Me Me resinous, 1/1 50 Ph iPr H A-1 Cl Me Me 132-133 51 PhiPr COtBu A-1 Cl Me Me resinous, 1/1 52 Ph CH₂OMe COtBu A-1 Cl Me Me36.4-42.3, 2/1 53 Ph Me Me A-1 Cl Me Me 123.1-125.1, E-form 54 Ph MeCH₂OEt A-1 Cl Me Me resinous, 1/1 55 Ph Me SO₂Ph A-1 Cl Me Me140.1-141.7, E-form 56 Ph Me CO₂iBu A-1 Cl Me Me resinous, 3/2 57 Ph MeCO(2-Cl—Ph) A-1 Cl Me Me 123.6-131.9, 4/3 58 Ph Me SO₂Me A-1 Cl Me Meresinous, 1/1 59 Ph Me CO(2- A-1 Cl Me Me 178.2-180.9, pyridyl) E-formor Z-form 60 Ph Me CO(2- A-1 Cl Me Me resinous, Z-form or E-formpyridyl) 61 2-MeO—Ph Me H A-1 Cl Me Me 128-130 62 2-MeO—Ph Me COtBu A-1Cl Me Me resinous, 3/2 63 2-MeO—Ph Me H A-1 Me Me Me 100-111 64 2-MeO—PhMe COtBu A-1 Me Me Me 135-137, E-form or Z-form 65 2-MeO—Ph Me COtBu A-1Me Me Me resinous, Z-form or E-form 66 Ph nHex H A-1 Cl Me Me 109-110 67Ph nHex COtBu A-1 Cl Me Me resinous 68 Ph Me COtBu A-1 Cl Me Me 96-96.5,Z-form or E-form 69 1-naphthyl Me H A-1 Cl Me Me resinous 70 1-naphthylMe COtBu A-1 Cl Me Me resinous, 3/7 71 2-Ph—Ph Me H A-1 Cl Me Meresinous 72 2-Ph—Ph Me COtBu A-1 Cl Me Me resinous, E-form/Z-formmixture 73 2-CF₃—Ph Me H A-1 Cl Me Me resinous 74 2-CF₃—Ph Me COtBu A-1Cl Me Me resinous, E-form/Z-form mixture 75 2,6-F₂—Ph Me H A-1 Cl Me Meresinous 76 2,6-F₂—Ph Me COtBu A-1 Cl Me Me resinous, 5/4 77 Ph H COtBuA-1 Cl Me Me 119-120, E-form or Z-form 78 tBu H COtBu A-1 Cl Me Meresinous 79 tBu Me COtBu A-3 Me Me — resinous, Z-form or E-form 80 tBuMe COtBu A-3 Me Me — 111-113, E-form or Z-form 81 Ph Me COtBu A-2 Me HMe 128-137, E-form/Z-form mixture 82 Ph Me COtBu A-3 Me Me — 143-144,E-form or Z-form 83 Ph Me COtBu A-3 Me Me — 136-138.5 84 Ph H COtBu A-3Me Me — 104-105, Z-form or E-form 85 2-Cl—Ph Me H A-1 Cl Et Me resinous86 2-Cl—Ph Me COtBu A-1 Cl Et Me resinous, 1/1 87 Ph iPr H A-1 Me Me Meresinous 88 Ph nPr H A-1 Me Me Me resinous 89 Ph iPr COtBu A-1 Me Me Me125-125.5, Z-form 139-140, E-form 90 Ph nPr COtBu A-1 Me Me Me resinous,1/2 91 Ph nBu COtBu A-1 Me Me Me resinous, 1/1 92 Ph nBu COtBu A-3 Me Me— resinous, 1/1 93 Ph Et COtBu A-3 Me Me — resinous, 1/1 94 Ph Et COtBuA-1 Me Me Me 139-140, Z-form 119, E-form 95 Ph nBu H A-1 Me Me Meresinous 96 Ph nBu H A-3 Me Me — 111-113 97 2-Me—Ph Me COtBu A-3 Me Me —resinous 98 2-Me—Ph Me COCH₂Ph A-3 Me Me — resinous 99 Ph nBu COCH₂PhA-1 Me Me Me resinous, 1/2 100 Ph cHex H A-3 Me Me — 104-106 101 Ph cHexCOtBu A-3 Me Me — 128-130, E-form or Z-form 102 Ph cHex H A-1 Me Me Meresinous 103 Ph cHex COtBu A-1 Me Me Me resinous, 1/1 104 Ph Ph H A-1 MeMe Me resinous 105 Ph Ph COtBu A-1 Me Me Me resinous, 1/1 106 Ph H H A-1Cl Me Me 146-147 107 Ph Et H A-1 Me Me Me 112-115 108 Ph CH₂OEt H A-1 MeMe Me resinous 109 Ph CH₂OEt COtBu A-1 Me Me Me 52.1-55.3 110 Ph CH₂OnBuH A-1 Me Me Me resinous 111 Ph CH₂OnBu COtBu A-1 Me Me Me resinous, 1/1112 Ph iPr CO(3- A-1 Cl Me Me resinous pyridyl) 113 Ph iPr CO₂Et A-1 ClMe Me resinous, 2/1 114 Ph iPr CH₂OMe A-1 Cl Me Me resinous, 2/1 115 PhCH₂(N- H A-1 Me Me Me 142.3-145.9 morpholinyl) 116 Ph CH₂(N- COtBu A-1Me Me Me resinous, 4/1 morpholinyl) 117 Ph Et H A-6 F H — 144.5-145.5118 Ph Et COtBu A-6 F H — resinous, 1/1 119 Ph Et H A-6 F F —165.5-166.5 120 Ph Et COtBu A-6 F F — resinous, 2/1 121 Ph CH₂OCH₂— HA-1 Me Me Me resinous CH₂OMe 122 Ph CH₂OCH₂— COtBu A-1 Me Me Me resinousCH₂OMe 123 2-pyridyl Me COtBu A-1 Me Me Me resinous, E-form or Z-form124 2-pyridyl Me COtBu A-1 Me Me Me 134-135, Z-form or E-form 1252-pyridyl Me H A-1 Me Me Me 341 (decomp.) 126 2-pyridyl Me H A-6 F F —346.1 127 2-pyridyl Me COtBu A-6 F F — 111-112 128 Ph CH₂(N- H A-1 Me MeMe 182.6-185.1 pyrazolyl) 129 Ph CH₂(N- COtBu A-1 Me Me Me 133.3-135.8,9/1 pyrazolyl) 130 Ph CH₂(N- COtBu A-1 Me Me Me resinous, 1/4 pyrazolyl)131 Ph Et CO(A-1) A-1 Me Me Me 145-145.5 132 Ph iPr H A-3 Me Me —90.1-92.5 133 Ph iPr H A-3 CF₃ Me — 106.3-108.9 134 Ph iPr COtBu A-3 MeMe — resinous, 1/1 135 Ph iPr COtBu A-3 CF₃ Me — resinous, 2/1 136 Ph EtCOtBu A-1 CN Me Me resinous 137 Ph Et H A-1 CN Me Me 129-130 138 Ph Et HA-7 Cl H Me 112-114 139 Ph Et COtBu A-7 Cl H Me resinous, 5/4

[Test Example]

Now, the following Test Examples are to demonstrate the usefulness ofthe compounds of the present invention as pesticides.

[Test Example 1] Acaricidal Test For Two-spotted Spider Mites(Tetranychus urticae)

The leaves of kidney bean plants were punched into 3.0 cm-diameterdiscs, using a leaf punch, and put onto moistured filter paper in a 7cm-diameter styrol cup. Ten larvae of two-spotted spider mites(Tetranychus urticae) were put to each leaf. A 5% emulsion (or 25%wettable powder) of a compound of the invention was diluted with watercontaining a spreading agent to give a 500 ppm solution of the compound.The solution was sprayed over each cup in an amount of 2 ml/cup, using arotary sprinkler, and the cups were stored in a thermostatic chamber at25° C. After 96 hours passed, the mites in each cup were observed, andmortality of the mites was determined according to the followingequation. Each compound was tested in that manner for two groups ofdishes.

Mortality (%)=[number of insect killed/(number of insect killed+numberof living insect)]×100

In this test, the following compounds exhibited mortality of 80% ormore: Compounds of the invention: Nos. 1-24, 26-30, 32-38, 40-52, 54-60,62, 65-80, 82-124 and 127-136.

TEST EXAMPLE 2 Residual Effect Test for Citrus Red Mite (Panonychuscitri)

A 5% emulsion (or 25% wettable powder) of a compound of the inventionwas diluted with water containing a spreading agent to give a solutionof the compound with prescribed concentration. The solution was sprayedover each orange planted in a pot in an amount of 250 ml/pot, using arotary sprinkler, and the pot were left in the open air. After theprescribed days, the leaves of orange plants were punched into 3.0cm-diameter discs, using a leaf punch, and put onto moistured filterpaper in a 7 cm-diameter styrol cup. Ten larvae of citrus red mite(Panonychus citri) were put to each leaf. Then, the cups were stored ina thermostatic chamber at 25° C. After 48 hours passed, the mites ineach cup were observed, and mortality of the mites was determinedaccording to the same equation as in Test Example 1. Each compound wastested in that manner for four groups of dishes. The results are shownin Tables 4-7 below.

In the test, the following Compound A described in WO97/40009 was usedas a comparative compound.

In the test, the following Compound A described in WO97/40009 was usedas a comparative compound.

TABLE 4 Concentration Mortality (%) of spray Days left in the open airafter spraying Compound solution the solution to orange planted in a potNo. (ppm) 2 4 7 9 11 13 17 19 22 26 29 4 100 100 100 100 100 100 100 100100 100 100 92.5 5 100 100 100 100 100 100 100 100 100 100 100 100 7 100100 100 100 100 90.0 47.5 57.5 — — — — 9 100 100 100 100 100 97.5 32.5 —— — — — 21 100 100 100 100 100 100 100 95.0 100 60.0 100 67.5 A 100 17.540.0 — — — — — — — — —

TABLE 5 Concentration Mortality (%) of spray Days left in the open airafter spraying Compound solution the solution to orange planted in a potNo. (ppm) 2 4 6 10 14 16 18 22 33 100 100 100 100 100 100 97.5 100 87.535 100 100 100 100 100 100 95.0 82.5 67.5 A 100 17.5 40.0 — — — — — —

TABLE 6 Concentration Mortality (%) of spray Days left in the open airafter spraying Compound solution the solution to orange planted in a potNo. (ppm) 2 4 5 8 12 14 16 20 41 100 100 — 100 100 100 95.0 97.5 52.5 76100 100 — 77.5 52.5 — — — — A 100 17.5 40.0 — — — — — —

TABLE 7 Concentration Mortality (%) of spray Days left in the open airafter spraying Compound solution the solution to orange planted in a potNo. (ppm) 2 4 5 7 9 13 15 89^(*1) 100 100 92.5 100 100 100 100 52.5 9050 100 100 100 100 100 65.0 27.5 91 100 100 100 100 100 100 100 37.5 9250 100 97.5 100 92.5 92.5 45.0 — 93 100 100 100 100 100 100 50.0 40.094^(*2) 50 100 100 100 100 100 90.0 52.5 A 100 17.5 40.0 — — — — —^(*1)A mixture of an equal amount of Z-form and E-form ^(*2)Z-form

Industry Applicability

The present invention provides novel insecticides and acaricides havinglong-term residual effect.

What is claimed is:
 1. Acrylonitrile compounds of formula (1):

wherein, R of a C₁-C₆ alkyl, a C₃-C₇ cycloalkyl optionally substitutedby a C₁-C₄ alkyl, a phenyl optionally substituted by X, a naphthyl or apyridyl, R¹ is H, a halogen, a C₁-C₆ alkyl, a C₃-C₇ cycloalkyloptionally substituted by a C₁-C₆ alkoxy, a C₁-C₄ haloalkyl, a C₂-C₆alkoxyalkyl, CH₃OC₂H₄OCH₂, a C₂-C₆ alkylsulfenylalkyl, a C₂-C₆alkylsulfinyalkyl, a C₂-C₆ alkylsulonylalkyl, a C₁-C₃alkyl substitutedby phenyl, a phenyl, C₇-C₁₀ phenoxyalkyl, COORa, CONHRb, CONRaRb, CORa,CO(piprridyl), CN, NO₂ or CH₂J, A is

B is H, a C₁-C₄ alkyl, a C₂-C₄ alkoxyalkyl, CH₂SCH₃, CH₂OC₂H₄OCH₃, aC₁-C₄ alkyl substituted by Rc or Rd, a tetrahydropyranyl, Si(CH₃)₃,SO₂Re, SO₂NHRb, SO₂NRaRb, C(S)NHRb, C(S)NRaRb, CH₂COORa, C(O)Rf,P(O)RgRh, P(S)RgRh, an alkali metal, an alkaline earth metal orNHRiRjRk, X is one to three substitutes as freely selected from ahalogen, a C₁-C₄alkyl, a C₁-C₄ haloalkyl, a C₁-C₄ alkoxy, a C₁-C₄alkylsulfenyl, a C₁-C₄ alkylsulfinyl, a C₁-C₄ alkylsulfonyl, a C₁-C₄haloalkylsulfenyl, a C₁-C₄ haloalkylsulfinyl, a C₁-C₄ haloalkylsulfonyl,NO₂, CN, a phenyl and a phenoxy, Y, Y₁ and y₂ are each independently ofeach other H, a halogen, C₁-C₄ alkyl, a C₁-C₄ haloalkyl, a C₁-C₄ alkoxy,a C₁-C₄ haloalkyoxy, a C₁-C₄ alkylsulfenyl, C₁-C₄ alkylsulfinyl, a C₁-C₄alkylsulfonyl, a C₁-C₄ haloalkylsulfenyl, a C₁-C₄ haloalkylsulfinyl, aC₁-C₄ haloalkylsulfonyl, NO₂ or CN, Y₃ is a C₁-C₄ alkyl or a C₁-C₄haloalkyl, Ra is a C₁-C₆ alkyl, Rb is H, a C₁-C₆ alkyl, or a phenyloptionally substituted by T¹, Rc is a phenyl optionally substituted byon or more substituents as freely selected from a halogen, a C₁-C₄alkyl, a C₁-C₄ alkoxy and a C₁-C₄ haloalkyl Rd is a benzoyl optionallysubstituted by on or more substituents as freely selected from ahalogen, a C₁-C₄ alkyl, and a C₁-C₄ haloalkyl, Re is a C₁-C₄ alkyl, aC₁-C₄ haloalkyl, or a phenyl optionally substituted by T¹, Rf is C₁-C₆alkyl, a C₂-C₆ alkenyl, a C₁-C₆ halogalkyl, a C₂-C₄ alkxyalkyl, a C₃-C₆halocycloalkyl, a C₁-C₄ alkyl substituted by Rc, a C₃-C₇ cycloalkyloptionally substituted by a C₁-C₄ alkyl, a cycloalkyl substituted by Rc,a cyclopropyl nsubstituted by Rc and a C₁-C₄ alkyl, a C₃-C₄ cycloalkylsubstituted by Rc and a halogen, a cyclopropyl substituted by T² and aC₁-C₄ alkyl, a C₂-C₄ alkenl subsituted by Rc, a C₁-C₆ alkoxy, a C₁-C₄haloalkoxy, a C₂-C₅ alkenyloxy, a C₃-C₆ cycloalkoxy optionallysubstituted by a C₁-C₃ alkyl, a benzyloxy, COORa, —NU¹NU², a phenyloptionally substituted by T³, a naphthyl, a pyridly optionallysubstituted by T¹, a phenyl C₁-C₆ alkyl or A-3, Rg and Rh are eachindepenently of the other OH, a phenyl a C₁-C₆ alkyl, a C₁-C₆ alkoxy ora C₁-C₄ alkylsulfenyl, Ri, Rj and Rk are each indepentently of the otherH, a C₁-C₆ alkyl, a C₁-C₄ alkenyl, a C₃-C₆ cycloalkyl optionallysubstituted by a C₁-C₃ alkyl or a benzyl, or any two of Ri, Rj and Rkmay, together with the nitrogen atom to which ther are bonded, for a 5-or 8-membered ring group optionally containg an oxygen atom, a ntitogenatom or a sulfer atom, J is a pyrazolyl, an imidazolyl or a morpholinyl,T¹ is a halogen, a C₁-C₄ alkyl, a C₁-C₄ haloalkyl or a C₁-C₄ alkoxy, T²is a C₂-C₄ alkenyl optionally substituted by a halogen, T³ is one offive substituents as freely selected from a halogen, C₁-C₄ alkyl, aC₁-C₄ haloalkyl, a C₁-C₄ alkoxy, C₁-C₄ alkylsulfenyl, a C₁-C₄alkylsulfinyl, a C₁-C₄ alkylsulfonyl, a C₁-C₄ haloalkylsulfenyl, a C₁-C₄haloalkylsulfinyl, a C₁-C₄ haloalkylsulfonyl, NO₂, CN, CHO, —NU¹U², aphenyl and a phennoxy, U¹ and U² are each independently of the other H,a C₁-C₆ alkyl, COORa, a phenyl or a benyzl, or U¹ and U² may, togetherwith the nitrogen atom to which thay are bonded, from a 5- to 8-memberedring group optionally containg an oxygen atom, a nitrogen atom or asulfer atom, m represents the number of substituents, and is 0, 1, 2 or3, n represents the number of substituents, and is 0, 1, 2, 3 or 4, prepresents the number of substituents, and is 0, 1 or 2, q representsthe number of substituents, and is 0 or 1, (provided that when m, n or pis 2 or more, then the substituents may be the same or different). 2.Acrylonitrile compounds according to claim 1, wherein R is

 1-naphtyl, tertiary butyl or 2-pyridyl, X₁ is H, a halogen, a C¹-C₄alkyl, a C¹-C₄ alkoxy, a C¹-C₄ haloalkyl or a phenyl, X₂ is H or ahalogen, R¹ is H, a C₁-C₆ alkyl, a C₃-C₇ cycloalkyl, CN, COORa,CO(N-piperidyl), a C₂-C₆ alkylsulfenylalkyl, a C₂-C₆ alkoxyalkyl,CH₃OC₂H₄OCH₂, CONRaRb, a phenyl or CH₂J, A is A-3, B is H, a C¹-C₄alkyl, C(O)Rf, SO₂Re or a C₂-C₄ alkoxyalkyl, Ra and Rb are eachindependently of the other a C¹-C₆ alkyl, Rf is a C₁-C₆ alkyl, a C₁-C₆alkoxy, a phenyl optionally substituted by a halogen, 2-pyridyl,3-pyridyl, a phenyl C₁-C₆ alkyl or 5-pyrazolyl substituted by a C₁-C₄alkyl, Re is a C₁-C₄ alkyl or a phenyl, Y₁ and Y₂ are each independentlyof the other H, a halogen, a C₁-C₄ alkyl, a C¹-C₄ haloalkyl or CN, Y₃ isa C¹-C₄ alkyl, and J is an N-pyrazolyl or N-morpholinyl. 3.Acrylonitrile compounds according to claim 2, wherein, R is

X₁ is H, a halogen or a C₁-C₄ alkyl, R¹ is H, a C₁-C₆ alkyl or a C₃-C₇cycloalkyl, A is A-3, B is H or C(O)Rf, Rf is a C₁-C₆ alkyl, a phenyl ora phenyl C₁-C₆ alkyl, Y₁ is a C₁-C₄ alkyl or a C₁-C₄ haloalkyl, and Y₂is a C₁-C₄ alkyl.
 4. Acrylonitrile compounds according to claim 3,wherein X₁ is H, a chlorine atom or methyl, R¹ is H, methyl, ethyl,isopropyl, normal butyl or cyclohexyl, B is H or C(O)Rf, Rf is tertiarybutyl, a phenyl or a benzyl, Y₁ is methyl or trifluoromethyl, and Y₂ ismethyl.
 5. Acrylonitrile compounds according to claim 3, wherein X₁ isH, R¹ is a C₁-C₆ alkyl, B is C(O)Rf, Rf is a C₁-C₆ alkyl, Y₁ is a C₁-C₄alkyl, and Y₂ is a C¹-C₄ alkyl.
 6. Acrylonitrile compounds according toclaim 5, wherein X₁ is H, R¹ is methyl, ethyl, isopropyl or normalbutyl, B is C(O)Rf, Rf is tertiary butyl, Y₁ is methyl, and Y₂ ismethyl.
 7. An agricultural chemical characterized by comprising, as anactive ingredient, one or more acrylonitrile compounds according toclaim
 1. 8. An agricultural chemical characterized by comprising, as anactive ingredient, one or more acrylonitrile compounds according toclaim
 2. 9. An agricultural chemical characterized by comprising, as anactive ingredient, one or more acrylonitrile compounds according toclaim
 3. 10. An agricultural chemical characterized by comprising, as anactive ingredient, one or more acrylonitrile compounds according toclaim
 4. 11. An agricultural chemical characterized by comprising, as anactive ingredient, one or more acrylonitrile compounds according toclaim
 5. 12. An agricultural chemical characterized by comprising, as anactive ingredient, one or more-acrylonitrile compounds according toclaim 6.